Pyridinecarboxamides, useful-plant-protecting composition comprising them and processes for their prepartion and their use

ABSTRACT

Compounds of the formula (I), or salts thereof, 
     
       
         
         
             
             
         
       
     
     in which R 1  to R 4  are as defined in formula (I) of claim  1  are suitable as useful-plant-protecting agents for reducing or preventing harmful effects of agrochemicals on the useful plants and their method of preparation are described.

INCORPORATION BY REFERENCE

This application claims benefit under 35 U.S.C. 119(a) of Europeanpatent application 07400013.4, filed on 30 Apr. 2007.

Any foregoing applications, including European patent application EP07400013.4, and all documents cited therein or during their prosecution(“application cited documents”) and all documents cited or referenced inthe application cited documents, and all documents cited or referencedherein (“herein cited documents”), and all documents cited or referencedin herein cited documents, together with any manufacturer'sinstructions, descriptions, product specifications, and product sheetsfor any products mentioned herein or in any document incorporated byreference herein, are hereby incorporated herein by reference, and maybe employed in the practice of the invention.

DESCRIPTION

The present invention relates to useful-plant-protecting compounds andcompositions comprising specific compounds as safeners for reducingphytotoxic actions of agrochemicals, in particular of herbicides. Theinvention relates in particular to pyridone derivatives as safeners andto processes for their preparation.

When controlling unwanted organisms in crops of plants which are usefulfor agriculture or forestry by using pesticides, the useful plants arefrequently also damaged to a greater or lesser extent, by the pesticidesemployed. This unwanted phytotoxic effect is encountered in particularwith the use of a considerable number of herbicides in crops of usefulplants such as, for example, corn, rice or cereals—and there primarilyin the post-emergence application. In some instances, the useful plantscan be protected against the phytotoxic properties of the pesticides byemploying safeners or antidotes, without diminishing or substantiallyimpairing the pesticidal activity against the harmful organisms. In somecases, even an improved pesticidal action against harmful organisms suchas weeds was observed.

The compounds hitherto known as safeners belong to a large number ofdifferent chemical structure classes, their suitability as safenersgenerally also depending on the chemical structures of the pesticidesand on the crops of useful plants.

Known for a long time have been the safener actions of compounds fromthe group of the phenoxy- or heteroaryloxyalkanecarboxylic acids,provided these compounds are applied in combination with herbicides.Examples of such compounds are MCPA and similar compounds which are atthe same time herbicidally active against harmful plants, orcloquintocet-mexyl.

Known are furthermore safeners from the group of the derivatives ofN-phenyl-substituted heteroaromatic carboxylic esters having a pluralityof heteroatoms in the heterocycle. Examples of such safeners are thesafeners mefenpyr-diethyl and isoxadifen-ethyl, which are used incommercial products.

WO 2004/084631 (us 2004-0224844) discloses the use ofhydroxyl-substituted aromatic carboxylic acid derivatives. WO2005/015994 (US 2005-037922) describes specific derivatives of salicylicacid as safeners. These compounds are suitable in particular for use assafeners in crops of corn and soybeans.

Furthermore, WO 2005/112630 (US 2005-256000) discloses1,2-dihydroquinoxalin-2-one derivatives as safeners.

Active compounds from the chemical class of the pyridones withpesticidal properties are known from the literature. Various biologicalactions are described; thus, for example, WO 2001/014339 (US2002-177578) describes the fungicidal action of certain substitutedpyridonecarboxamides, WO 2005/042492 (US 2007-196406) and WO 2005/042493(US 2007-037858) describe inter alia the fungicidal action ofheterocyclylcarboxanilides. EP-A-544151 (U.S. Pat. No. 5,344,813)describes the action of hydroxyl-substituted pyridonecarboxamides asherbicides. Also known are representatives having pharmacologicalproperties. Thus, WO 2001/055115 (U.S. Pat. No. 6,794,397) describesnicotinanilides as inductors of apoptosis, and US 2004/0116479 describesdialkylnicotinamides as inhibitors of angiogenesis.

Furthermore, EP-A-522392 (U.S. Pat. No. 5,232,060) describes6-trifluoromethyl-substituted pyridonecarboxamides as precursors for thesynthesis of herbicidally active sulfonylureas. Helv. Chim. Acta 71(1988) 596-601 and GB 2305174 mention1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide,6-chloro(difluoro)methyl-1,2-dihydro-2-oxopyridine-3-carboxamide and6-difluoromethyl-1,2-dihydro-2-oxo-pyridine-3-carboxamide asintermediates in the synthesis of pyranopyridines. WO 2007/041052mentions 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide as anintermediate in the synthesis of pharmacologically activespiropiperidines.

The use of such compounds as safeners in combination with certainpesticides has hitherto not been disclosed.

WO 2006/007981 (US 2007-265164) describes a method for identifyingcompounds which induce the defense of plants against pathogens, wherethe increase of the expression of plant-endogenous genes is consideredto be an indication for the induction.

Here, 1,2-dihydro-2-oxo-6-trifluoromethylpyridine-3-carboxamide ismentioned as part of a group of six compounds which may be referred toas safeners. A safener action confirmed by biological tests on plantshas hitherto not been disclosed for this compound, and is also notsufficiently disclosed by WO 2006/007981.

In particular the expression values obtained according to WO 2006/007981for the compound, which in some cases are at a considerably lower levelthan those for commercially available safeners also mentioned, lead itto be expected in the best case that, as safeners, they are considerablyless suitable, if at all.

When safeners were used to protect useful plants against damage bypesticides, it was found that the known safeners may in many cases havedisadvantages. These include:

-   -   the safener reduces the efficacy of the pesticides, in        particular that of herbicides, against the harmful plants,    -   the useful-plant-protecting properties are insufficient,    -   in combination with a certain herbicide, the spectrum of the        useful plants in which the safener/herbicide is to be employed        is not sufficiently wide,    -   a certain safener can only be combined with a small number of        herbicides,    -   by using safeners, the application rate to be applied and the        amount of formulation is increased, which may cause problems        during the application.

For the reasons mentioned, there is a need to provide alternativecompounds having safener action.

The invention provides the use of compounds of the formula (I) or saltsthereof

in which

-   R¹ is a (C₁-C₆)-haloalkyl radical, preferably a radical of the    formula CF₃, CF₂Cl, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃,    CFHCF₃, CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃, or C(CH₃)₂F and-   R² is hydrogen or halogen and-   R³ is hydrogen, (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or    (C₂-C₁₆)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,        [(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which is        unsubstituted or substituted, phenyl, which is unsubstituted or        substituted, and heterocyclyl, which is unsubstituted or        substituted,-    or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring,    -   where each of the 4 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,        [(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,        (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted,        phenyl, which is unsubstituted or substituted, and heterocyclyl,        which is unsubstituted or substituted,-    and-   R⁴ is (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or (C₂-C₁₆)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,        [(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which is        unsubstituted or substituted, phenyl, which is unsubstituted or        substituted, and heterocyclyl, which is unsubstituted or        substituted-    or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring,    -   where each of the 4 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,        [(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,        (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted,        phenyl, which is unsubstituted or substituted, and heterocyclyl,        which is unsubstituted or substituted,-    or-   R³ is (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₆)-alkynyloxy or    (C₂-C₄)-haloalkoxy and-   R⁴ is hydrogen or (C₁-C₄)-alkyl or-   R³ and R⁴ together with the directly attached nitrogen atom are a    four- to eight-membered heterocyclic ring which, in addition to the    nitrogen atom, may also comprise further hetero ring atoms,    preferably up to two further hetero ring atoms selected from the    group consisting of N, O and S, and which is unsubstituted or    substituted by one or more radicals selected from the group    consisting of halogen, cyano, nitro, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and    (C₁-C₄)-alkylthio, or-   R³ and R⁴ together with the directly attached nitrogen atom are the    group —N═CR⁵—NR⁶R⁷, in which-    R⁵ is hydrogen or (C₁-C₆)-alkyl, with hydrogen being preferred, and-    R⁶, R⁷ independently of one another are hydrogen or (C₁-C₄)-alkyl,    preferably (C₁-C₂)-alkyl, or R⁶ and R⁷ together with the directly    attached nitrogen atom form a five- to seven-membered, preferably    saturated heterocyclic ring, such as, for example, piperidinyl,    pyrrolidinyl or morpholinyl,-    or-   R¹ is a (C₁-C₆)-haloalkyl radical, preferably a radical of the    formula CF₃, CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃,    CFHCF₃, CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃ or C(CH₃)₂F, more preferably a    radical of the formula CF₃, CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁,    CF₂CF₂CF₃ or C(CH₃)₂F, in particular CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H,    CF₂CF₂C₁, CF₂CF₂CF₃ or C(CH₃)₂F, even more preferably CF₂C₁, CF₂H,    CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁ or CF₂CF₂CF₃,-   R² is halogen,-   R³ is hydrogen and-   R⁴ is hydrogen-    or-   R¹ is a radical of the formula CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H,    CF₂CF₂Cl, CFClCF₃, CFHCF₃, CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃ or    C(CH₃)₂F, more preferably CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁,    CF₂CF₂CF₃ or C(CH₃)₂F, even more preferably CF₂C₁, CF₂H, CF₂CF₃,    CF₂CF₂H, CF₂CF₂C₁ or CF₂CF₂CF₃,-   R² is hydrogen,-   R³ is hydrogen and-   R⁴ is hydrogen,    as a useful-plant-protecting agent for reducing or preventing    harmful actions of agrochemicals, preferably pesticides, in    particular herbicides, on the useful plants.

Hereinbelow, the compounds of the formula (I) and their salts are insome cases also referred to as “compounds (I)” according to theinvention or used according to the invention.

The compounds of the formula (I) also include tautomers which can beformed by hydrogen shifts and whose structure is formally not embracedby the formula (I). These tautomers are nevertheless included in thedefinition of the compounds of the formula (I) according to theinvention. The definition of the compounds of the formula (I) includesin particular the tautomeric structures of the formula (Ia)(2-hydroxypyridine-3-carboxamides) or salts thereof

in whichR¹, R², R³ and R⁴ are as defined in formula (I).

Some compounds of the formula (I) according to the invention or saltsthereof are novel and also form part of the subject matter of theinvention.

It is noted that in this disclosure and particularly in the claimsand/or paragraphs, terms such as “comprises”, “comprised”, “comprising”and the like can have the meaning attributed to it in U.S. Patent law;e.g., they can mean “includes”, “included”, “including”, and the like;and that terms such as “consisting essentially of” and “consistsessentially of” have the meaning ascribed to them in U.S. Patent law,e.g., they allow for elements not explicitly recited, but excludeelements that are found in the prior art or that affect a basic or novelcharacteristic of the invention.

It is further noted that the invention does not intend to encompasswithin the scope of the invention any previously disclosed product,process of making the product or method of using the product, whichmeets the written description and enablement requirements of the USPTO(35 U.S.C. 112, first paragraph) or the EPO (Article 83 of the EPC),such that applicant(s) reserve the right and hereby disclose adisclaimer of any previously described product, method of making theproduct or process of using the product.

The invention also provides useful-plant-protecting compositionscomprising compounds of the formula (I) or salts thereof and formulationauxiliaries. The invention also provides useful-plant-protectingcompositions comprising compounds of the formula (I) or salts thereof incombination with further agrochemicals, preferably pesticides, inparticular herbicides, and, if appropriate, formulation auxiliaries.

Some compounds of the formula (I) are already described as intermediatesfor preparing active compounds, see the abovementioned GB-A-2305174(comp. (I) in which R¹═CF₃, CF₂C₁ or CF₂H and R³═R⁴═H). EP-A-522392,which has already been mentioned, described in a general manner interalia compounds (I) as intermediates for preparing sulfonylureas. Thesafener actions of the compounds have not been described.

The invention also provides compounds of the formula (I) or saltsthereof

-   in which-   R¹ is a (C₁-C₆)-haloalkyl radical, preferably a radical of the    formula CF₃, CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃,    CFHCF₃, CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃ or C(CH₃)₂F, in particular a    radical of the formula CF₃, CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁,    CF₂CF₂CF₃ or C(CH₃)₂F, more preferably CF₃, CF₂C₁, CF₂H, CF₂CF₃,    CF₂CF₂H, CF₂CF₂C₁ or CF₂CF₂CF₃-    and-   R² is hydrogen or halogen and-   R³ is hydrogen, (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or    (C₂-C₁₆)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl, and        [(C₁-C₄)-haloalkoxy]-carbonyl,-    or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring,    -   where each of the 4 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,        [(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,        (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted,        phenyl, which is unsubstituted or substituted, and heterocyclyl,        which is unsubstituted or substituted,-    and-   R⁴ is (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or (C₂-C₁₆)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl, and        [(C₁-C₄)-haloalkoxy]-carbonyl,-    or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring,    -   where each of the 4 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,        [(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,        (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted,        phenyl, which is unsubstituted or substituted, and heterocyclyl,        which is unsubstituted or substituted,-    or-   R³ is (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₆)-alkynyloxy or    (C₂-C₄)-haloalkoxy and-   R⁴ is hydrogen or (C₁-C₄)-alkyl or-   R³ and R⁴ together with the directly attached nitrogen atom are a    four- to eight-membered heterocyclic ring which, in addition to the    nitrogen atom, may also comprise further hetero ring atoms,    preferably up to two further hetero ring atoms selected from the    group consisting of N, O and S, and which is unsubstituted or    substituted by one or more radicals selected from the group    consisting of halogen, cyano, nitro, (C₁-C₄)-alkyl,    (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and    (C₁-C₄)-alkylthio, or-   R³ and R⁴ together with the directly attached nitrogen atom are the    group —N═CR⁵—NR⁶R⁷ in which-    R⁵ is hydrogen or (C₁-C₆)-alkyl, with hydrogen being preferred, and-    R⁶, R⁷ independently of one another are hydrogen or (C₁-C₄)-alkyl,    preferably (C₁-C₂)-alkyl, or R⁶ and R⁷ together with the directly    attached nitrogen atom form a five- to seven-membered, preferably    saturated heterocyclic ring, such as, for example, piperidinyl,    pyrrolidinyl or morpholinyl,-    or-   R¹ is a (C₁-C₆)-haloalkyl radical, preferably a radical of the    formula CF₃, CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃,    CFHCF₃, CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃ or C(CH₃)₂F, more preferably    CF₃, CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁, CF₂CF₂CF₃ or C(CH₃)₂F,    in particular CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁, CF₂CF₂CF₃ or    C(CH₃)₂F, even more preferably CF₂C₁, CF₂CF₃, CF₂CF₂C₁ or CF₂CF₂CF₃,-   R² is halogen,-   R³ is hydrogen and-   R⁴ is hydrogen-    or-   R¹ is a radical of the formula CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃,    CFHCF₃, CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃ or C(CH₃)₂F, preferably    CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃, CF₂CF₂CF₃ or C(CH₃)₂F, in    particular CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃ or CF₂CF₂CF₃, even    more preferably CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁ or CF₂CF₂CF₃,-   R² is hydrogen,-   R³ is hydrogen and-   R⁴ is hydrogen.

Preferably excluded are compounds of the formula (I) and salts thereofin which

R¹ is (C₁-C₃)-alkyl which is substituted by one to three fluorine atoms,R² is hydrogen,R³ is (C₁-C₂)-alkyl andR⁴ is (C₁-C₂)-alkyl.

The last mentioned preferably excluded compounds are described in ageneral manner in the abovementioned EP-A-0522392 as intermediates forpreparing sulfonylureas.

Depending on the nature and the attachment of the substituents, thecompounds of the formula (I) may be present as stereoisomers. Allpossible stereoisomers defined by their specific spatial form, such asenantiomers, diastereomers, Z- and E-isomers, are embraced by theformula (I).

If, for example, one or more alkenyl groups are present, it is possiblefor diastereomers (Z- and E-isomers) to occur. If, for example, one ormore asymmetric carbon atoms are present, it is possible for enantiomersand diastereomers to occur. Stereoisomers can be obtained by customaryseparation methods, for example by chromatographic separationprocedures, from the mixtures obtained in the preparation. It is alsopossible to selectively prepare stereoisomers by employingstereoselective reactions using optically active starting materialsand/or auxiliaries. Thus, the invention also relates to allstereoisomers embraced by the formula (I) but not shown in theirspecific stereoform and mixtures thereof.

The possibilities of combining the various substituents of the formula(I) are to be understood in such a way that the general principles ofthe synthesis of chemical compounds are to be observed, i.e. the formula(I) does not embrace compounds which the skilled worker knows to bechemically impossible.

The terms used above and further below are familiar to the personskilled in the art and have in particular the meanings illustratedbelow:

The term “(C₁-C₄)-alkyl” is a short notation for open-chain alkyl having1 to 4 carbon atoms corresponding to the stated range of carbon atoms,i.e. it includes the radicals methyl, ethyl, 1-propyl, 2-propyl,1-butyl, 2-butyl, 2-methylpropyl and tert-butyl. Correspondingly,general alkyl radicals having a wider stated range of carbon atoms, forexample “(C₁-C₆)-alkyl”, also include straight-chain or branched alkylradicals having a larger number of carbon atoms, i.e. in the examplealso the alkyl radicals having 5 and 6 carbon atoms.

Unless specifically indicated, the lower carbon skeletons, for examplethose having 1 to 6 carbon atoms or, in the case of unsaturated groups,having 2 to 6 carbon atoms, are preferred for the hydrocarbon radicalssuch as alkyl, alkenyl and alkynyl radicals, including in compositeradicals. Alkyl radicals, including in the composite meanings, such asalkoxy, haloalkyl, etc., are, for example, methyl, ethyl, n- orisopropyl, n-, iso, t- or 2-butyl, pentyls, hexyls, such as n-hexyl,isohexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyland 1,4-dimethylpentyl; alkenyl and alkynyl radicals have the meaningsof the possible unsaturated radicals which correspond to the alkylradicals; alkenyl is, for example, vinyl, allyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 2-butenyl, pentenyl, 2-methylpentenyl or hexenyl,preferably allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl,but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl or1-methylbut-2-en-1-yl. (C₂-C₆)-alkynyl is, for example, ethynyl,propargyl, 1-methyl-2-propynyl, 2-methyl-2-propynyl, 2-butynyl,2-pentynyl or 2-hexynyl, preferably propargyl, but-2-yn-1-yl,but-3-yn-1-yl or 1-methylbut-3-yn-1-yl.

Alkylidene, including, for example, in the form (C₁-C₁₀)-alkylidene, isthe radical of a straight-chain or branched alkane which is attached viaa double bond, where the position of the point of attachment has not yetbeen fixed. The only possible positions in the case of a branched alkaneare, of course, positions in which two hydrogen atoms may be replaced bythe double bond; radicals are, for example, ═CH₂, ═CH—CH₃, ═C(CH₃)—CH₃,═C(CH₃)—C₂H₅ or ═C(C₂H₅)—C₂H₅.

Cycloalkyl is a carbocyclic saturated ring system having preferably 3-8carbon atoms, for example cyclopropyl, cyclobutyl, cyclopentyl orcyclohexyl. Substituted cycloalkyl embraces cyclic systems havingsubstituents, substituents having a double bond at the cycloalkylradical, for example an alkylidene group, such as methylidene, alsobeing included. Substituted cycloalkyl also embraces polycyclicaliphatic systems, such as, for example, bicyclo[1.1.0]butan-1-yl,bicyclo[1.1.0]butan-2-yl, bicyclo[2.1.0]pentan-1-yl,bicyclo[2,1,0]pentan-2-yl, bicyclo[2.1.0]pentan-5-yl, adamantan-1-yl andadamantan-2-yl.

Cycloalkenyl is a carbocyclic, non-aromatic, partially unsaturated ringsystem having preferably 4-8 carbon atoms, for example 1-cyclobutenyl,2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or1,4-cyclohexadienyl. The explanations given for substituted cycloalkylapply correspondingly to substituted cycloalkenyl.

The term “halogen” denotes, for example, fluorine, chlorine, bromine oriodine. Haloalkyl, haloalkenyl and haloalkynyl are alkyl, alkenyl andalkynyl, respectively, which are partially or fully substituted byidentical or different halogen atoms, preferably from the groupconsisting of fluorine, chlorine and bromine, in particular from thegroup consisting of fluorine and chlorine, for example monohaloalkyl,such as CH₂CH₂Cl, CH₂CH₂F, CH₂ClCH₃, CH₂FCH₃, CH₂Cl, CH₂F; perhaloalkylsuch as CCl₃ or CF₃ or CF₃CF₂; polyhaloalkyl, such as CHF₂, CH₂F,CH₂FCHCl, CHCl₂, CF₂CF₂H, CH₂CF₃, CH₂ClCH₃, CH₂FCH₃; haloalkoxy is, forexample, OCF₃, OCHF₂, OCH₂F, CF₃CF₂O, OCH₂CF₃ and OCH₂CH₂Cl; thisapplies correspondingly to haloalkenyl and other halogen-substitutedradicals.

If a skeleton is substituted “by one or more radicals” from a list ofradicals (=group) or a generically defined group of radicals, thisincludes in each case the simultaneous substitution by a plurality ofidentical and/or structurally different radicals.

Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl,cycloalkyl, cycloalkenyl, phenyl, benzyl, heterocyclyl and heteroarylradical, are, for example, substituted radicals derived from anunsubstituted skeleton, the substituents being, for example, one ormore, preferably 1, 2 or 3, radicals from the group consisting ofhalogen, alkoxy, alkylthio, hydroxyl, amino, nitro, carboxyl, cyano,azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- anddialkylaminocarbonyl, substituted amino, such as acylamino, mono- anddialkylamino, trialkylsilyl and optionally substituted cycloalkyl,optionally substituted phenyl, optionally substituted heterocyclyl,where each of the last mentioned cyclic groups may also be attached viaheteroatoms or divalent functional groups as in the alkyl radicalsmentioned, and alkylsulfinyl, alkylsulfonyl and, in the case of cyclicradicals (=“cyclic skeleton”), also alkyl, haloalkyl, alkylthioalkyl,alkoxyalkyl, optionally substituted mono- and dialkylaminoalkyl andhydroxyalkyl; the term “substituted radicals”, such as substitutedalkyl, etc., includes as substituents, in addition to the saturatedhydrocarbon-containing radicals mentioned, the corresponding unsaturatedaliphatic and aromatic radicals, such as optionally substituted alkenyl,alkynyl, alkenyloxy, alkynyloxy, phenyl, phenoxy etc. In the case ofsubstituted cyclic radicals having aliphatic moieties in the ring, thisalso embraces cyclic systems having substituents which are attached tothe ring via a double bond, for example substituted by an alkylidenegroup, such as methylidene or ethylidene, or an oxo group, imino groupor substituted imino group.

The substituents mentioned by way of example (“first substituent level”)can, if they contain hydrocarbon-containing moieties, be, ifappropriate, substituted further in the moieties (“second substituentlevel”), for example by one of the substituents as defined for the firstsubstituent level. Corresponding further substituent levels arepossible. The term “substituted radical” preferably embraces only one ortwo substituent levels.

Preferred substituents for the substituent levels are, for example,

amino, hydroxyl, halogen, nitro, cyano, mercapto, carboxyl, carboxamide,SF₅, aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl,monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy,alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl,alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl,alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, alkylthio,cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio,alkylsulfinyl, alkylsulfonyl, monoalkylaminosulfonyl,dialkylaminosulfonyl, N-alkylaminocarbonyl, N,N-dialkyl-aminocarbonyl,N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy,benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino,heterocyclyl and trialkylsilyl.

In the case of radicals having carbon atoms, preference is given tothose having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, inparticular 1 or 2 carbon atoms. Preference is generally given tosubstituents selected from the group consisting of halogen, for examplefluorine and chlorine, (C₁-C₄)-alkyl, preferably methyl or ethyl,(C₁-C₄)-haloalkyl, preferably trifluoromethyl, (C₁-C₄)-alkoxy,preferably methoxy or ethoxy, (C₁-C₄)-haloalkoxy, nitro and cyano. Here,particular preference is given to the substituents methyl, methoxy,fluorine and chlorine.

Substituted amino, such as mono- or disubstituted amino, denotes aradical from the group of the substituted amino radicals which areN-substituted, for example, by one or two identical or differentradicals selected from the group consisting of alkyl, alkoxy, acyl andaryl; preferably mono- and dialkylamino, mono- and diarylamino,acylamino, N-alkyl-N-arylamino, N-alkyl-N-acylamino and saturatedN-heterocycles; here, preference is given to alkyl radicals having 1 to4 carbon atoms; aryl is preferably phenyl or substituted phenyl; foracyl, the definition given further down applies, preference is given to(C₁-C₄)-alkanoyl. This applies correspondingly to substitutedhydroxylamino or hydrazino.

Substituted amino also includes quaternary ammonium compounds (salts)with four organic substituents at the nitrogen atom.

Optionally substituted phenyl is preferably phenyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy and nitro, for example o-, m- and p-tolyl,dimethylphenyls, 2-, 3- and 4-chlorophenyl, 2-, 3- and 4-fluorophenyl,2-, 3- and 4-trifluoromethyl- and -trichloromethylphenyl, 2,4-, 3,5-,2,5- and 2,3-dichlorophenyl, o-, m- and p-methoxyphenyl.

Optionally substituted cycloalkyl is preferably cycloalkyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyland (C₁-C₄)-haloalkoxy, in particular by one or two (C₁-C₄)-alkylradicals.

Optionally substituted heterocyclyl is preferably heterocyclyl which isunsubstituted or mono- or polysubstituted, preferably up totrisubstituted, by identical or different radicals from the groupconsisting of halogen, (C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl,(C₁-C₄)-haloalkoxy, nitro and oxo, in particular mono- orpolysubstituted by radicals from the group consisting of halogen,(C₁-C₄)-alkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkyl and oxo, veryparticularly substituted by one or two (C₁-C₄)-alkyl radicals.

Acyl denotes a radical of an organic acid which, formally, is formed byremoving a hydroxyl group from the acid function, it also being possiblefor the organic radical in the acid to be attached to the acid functionvia a heteroatom. Examples of acyl are the radical —CO—R of a carboxylicacid HO—CO—R and radicals of acids derived therefrom, such asthiocarboxylic acid, unsubstituted or N-substituted iminocarboxylicacids or the radical of carbonic acid monoesters, N-substituted carbamicacid, sulfonic acids, sulfinic acids, N-substituted sulfonamido acids,phosphonic acids, phosphinic acids.

Acyl denotes, for example, formyl, alkylcarbonyl such as[(C₁-C₄)-alkyl]carbonyl, phenylcarbonyl, alkyloxycarbonyl,phenyloxycarbonyl, benzyloxycarbonyl, alkylsulfonyl, alkylsulfinyl,N-alkyl-1-iminoalkyl, N-alkyl- and N,N-dialkylcarbamoyl and otherradicals of organic acids. Here, the radicals may in each case besubstituted further in the alkyl or phenyl moiety, for example in thealkyl moiety by one or more radicals selected from the group consistingof halogen, alkoxy, phenyl and phenoxy; examples of substituents in thephenyl moiety are the substituents which have already been mentionedfurther above in a general manner for substituted phenyl.

Acyl denotes preferably an acyl radical in the narrower sense, i.e. aradical of an organic acid where the acid group is attached directly tothe carbon atom of an organic radical, for example alkanoyl, such asformyl and acetyl, aroyl, such as phenylcarbonyl, and other radicals ofsaturated or unsaturated organic acids.

“Aroyl” denotes an aryl radical as defined above which is attached via acarbonyl group, for example the benzoyl group.

If a general radical is defined as “hydrogen”, this means a hydrogenatom.

The “yl-position” of a radical denotes its point of attachment.

In accordance with the general definitions:

-   “(C₁-C₆)-alkyl” is a methyl, ethyl, propyl, isopropyl, 1-butyl,    2-butyl, 2-methylpropyl or tert-butyl radical;-   “(C₁-C₁₀)-alkyl” thus includes the alkyl radicals mentioned above,    and also isomeric pentyl radicals, such as n-pentyl,    1,1-dimethylpropyl or 2-methylbutyl, isomeric hexyl, heptyl, octyl,    nonyl or decyl radicals.-   Accordingly, “(C₂-C₄)-alkenyl” denotes, for example, the vinyl,    allyl, 2-methyl-2-propen-1-yl-, 2- or 3-buten-1-yl group,-   accordingly, “(C₃-C₁₀)-alkenyl” denotes, for example, the allyl,    2-methyl-2-propen-1-yl, 2- or 3-buten-1-yl, pentenyl,    2-methylpentenyl, hexenyl, heptenyl, octenyl, nonenyl or decenyl    group.-   “(C₂-C₄)-Alkynyl” denotes, for example, the ethynyl, propargyl or    2-butyn-1-yl group,-   “(C₃-C₁₀)-alkynyl” denotes, for example, the propargyl,    2-butyn-1-yl,-   2-pentyn-1-yl, 2-methylpentyn-3-yl, hexynyl, heptynyl, octynyl,    nonynyl or the decynyl group.

If the carbon chain of an alkyl radical is interrupted by more than oneoxygen atom, this means that two oxygen atoms must not be directlyadjacent.

-   “(C₃-C₆)-Cycloalkyl” denotes the cyclopropyl, cyclobutyl,    cyclopentyl or cyclohexyl radical,-   “(C₃-C₁₀)-cycloalkyl” denotes monocyclic alkyl radicals, such as the    cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl,    cyclooctyl or cyclodecyl radical, denotes bicyclic alkyl radicals,    such as the norbornyl or bicyclo[2.2.2]octyl radical, or denotes    fused systems, such as the decahydronaphthyl radical.-   “(C₄-C₁₀)-Cycloalkenyl” denotes monocyclic cycloalkylene radicals,    such as the cyclobutenyl, cyclopentenyl, cyclohexenyl,    cycloheptenyl, cyclooctenyl or cyclodecenyl radical, denotes    bicyclic alkyl radicals, such as the norbornenyl or    bicyclo[2.2.2]octenyl radical, or denotes fused systems, such as the    tetra-, hexa- or octahydronaphthyl radical.-   “(C₁-C₄)-Alkoxy” and “(C₁-C₁₀)-alkoxy” are alkoxy groups whose    hydrocarbon radicals have the meanings given under the terms    “(C₁-C₄)-alkyl” and “(C₁-C₁₀)-alkyl”.

In particular for reasons of better crop-plant- oruseful-plant-protecting action (safener action), better selectivityand/or better preparability, the use according to the invention ofcompounds of the formula (I) mentioned or salts thereof is of particularinterest in which individual radicals have one of the preferred meaningsalready mentioned or mentioned below, and in particular those whichcontain a combination of one or more of the preferred meanings alreadymentioned or mentioned below.

Preferably, if embraced by the above mentioned general definition offormula (I),

-   R¹ is a (C₁-C₄)-haloalkyl radical, more preferably CF₃, CF₂C₁, CF₂H,    CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, C(CH₃)₂F or CF₂CF₂CF₃, more preferably    CF₃, CF₂C₁, CF₂H, CF₂CF₂CF₃ or CF₂CF₃, more preferably CF₃, CF₂C₁,    CF₂CF₂CF₃ or CF₂CF₃, in particular CF₃, CF₂C₁ or CF₂CF₃.-   Preferably,-   R² is hydrogen or halogen. Here, halogen is preferably fluorine,    chlorine, bromine or iodine, in particular chlorine, bromine or    iodine, very particularly chlorine or bromine.-   Preferably,-   R³ is hydrogen, (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or    (C₂-C₁₀)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,        [(C₁-C₄)-haloalkoxy]-carbonyl,    -   (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted by one        or more radicals from the group consisting of halogen,        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, preferably unsubstituted or        substituted by (C₁-C₄)-alkyl,    -   phenyl, which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio, and    -   heterocyclyl, which is unsubstituted or substituted by one or        more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo, preferably        unsubstituted or substituted by one or more radicals from the        group consisting of (C₁-C₄)-alkyl (C₁-C₄)-haloalkyl and        (C₁-C₄)-alkoxy,-    or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring,    -   where each of the 4 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,        [(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,    -   (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted by one        or more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, preferably unsubstituted or        substituted by (C₁-C₄)-alkyl,    -   phenyl, which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio, and    -   heterocyclyl, which is unsubstituted or substituted by one or        more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo, preferably        unsubstituted or substituted by one or more radicals from the        group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl and        (C₁-C₄)-alkoxy,-    more preferably hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or    (C₂-C₆)-alkynyl, where each of the 3 last mentioned radicals is    unsubstituted or substituted by one or more radicals selected from    the group consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio and (C₁-C₄)-alkoxycarbonyl,-    more preferably hydrogen or (C₁-C₄)-alkyl, in particular hydrogen,    and-   R⁴ is (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,        [(C₁-C₄)-haloalkoxy]-carbonyl,    -   (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted by one        or more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, preferably unsubstituted or        substituted by (C₁-C₄)-alkyl,    -   phenyl, which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio, and    -   heterocyclyl, which is unsubstituted or substituted by one or        more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo, preferably        unsubstituted or substituted by one or more radicals selected        from the group consisting of (C₁-C₄)-alkyl (C₁-C₄)-haloalkyl and        (C₁-C₄)-alkoxy,-    or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl    which is condensed at one side of the ring to a 4- to 6-membered    saturated or unsaturated carbocyclic ring,    -   where each of the 4 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,        (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,        [(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,    -   (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted by one        or more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, preferably unsubstituted or        substituted by (C₁-C₄)-alkyl,    -   phenyl, which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio, and    -   heterocyclyl, which is unsubstituted or substituted by one or        more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo, preferably        unsubstituted or substituted by one or more radicals selected        from the group consisting of (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl        and (C₁-C₄)-alkoxy.

Here, heterocyclyl is preferably a heterocyclic 3- to 9-membered, inparticular 5- or 6-membered, ring having 1 to 3 hetero ring atoms fromthe group consisting of N, O and S.

More preferably,

-   R³ is hydrogen, (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or    (C₂-C₁₀)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,        [(C₁-C₄)-haloalkoxy]-carbonyl,    -   (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted by one        or more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, preferably unsubstituted or        substituted by (C₁-C₄)-alkyl,    -   phenyl, which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio, and    -   heterocyclyl, which is unsubstituted or substituted by one or        more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,-    or (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl which is condensed at    one side of the ring to a 4- to 6-membered saturated or unsaturated    carbocyclic ring,    -   where each of the 2 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of (C₁-C₄)-alkyl,-    more preferably hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or    (C₂-C₆)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio and (C₁-C₄)-alkoxycarbonyl,-    more preferably hydrogen or (C₁-C₄)-alkyl, in particular hydrogen,-   and-   R⁴ is as already defined above for R⁴ or preferably (C₁-C₁₀)-alkyl,    (C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,        [(C₁-C₄)-haloalkoxy]-carbonyl,    -   (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted by one        or more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, preferably unsubstituted or        substituted by (C₁-C₄)-alkyl,    -   phenyl, which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio, and    -   heterocyclyl, which is unsubstituted or substituted by one or        more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,-   or (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl which is condensed at    one side of the ring to a 4- to 6-membered saturated or unsaturated    carbocyclic ring,    -   where each of the 2 last mentioned radicals is unsubstituted or        substituted by one or more radicals from the group consisting of        (C₁-C₄)-alkyl.

More preferably.

-   R³ is hydrogen, (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or    (C₂-C₁₀)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio and [(C₁-C₄)-alkoxy]-carbonyl,-    preferably hydrogen, (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or    (C₂-C₆)-alkynyl, where each of the 3 last mentioned radicals is    unsubstituted or substituted by one or more radicals selected from    the group consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio and (C₁-C₄)-alkoxycarbonyl,    -    more preferably hydrogen or (C₁-C₄)-alkyl, in particular        hydrogen,-   and-   R⁴ is as already defined above for R⁴ or preferably    -    (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl, where        each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio and [(C₁-C₄)-alkoxy]-carbonyl,    -    preferably (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,        where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio and (C₁-C₄)-alkoxycarbonyl.

Particular preference is given to the use according to the invention ofcompounds of the formula (I) or salts thereof in which

-   R¹ is CF₃, CF₂C₁, CF₂H, CF₂CF₂CF₃ or CF₂CF₃, preferably CF₃, CF₂C₁,    CF₂CF₂CF₃ or CF₂CF₃, in particular CF₃, CF₂C₁ or CF₂CF₃ and-   R² is hydrogen or halogen, preferably hydrogen, and-   R³ is hydrogen, (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or    (C₂-C₁₀)-alkynyl, where each of the 3 last mentioned radicals is    unsubstituted or substituted by one or more radicals selected from    the group consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,    (C₁-C₄)-alkylthio and (C₁-C₄)-alkoxycarbonyl, preferably hydrogen,    (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl, where each of the    3 last mentioned radicals is unsubstituted or substituted by one or    more radicals selected from the group consisting of (C₁-C₄)-alkoxy,    (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and (C₁-C₄)-alkoxycarbonyl, in    particular hydrogen or (C₁-C₄)-alkyl, and-   R⁴ is (C₁-C₁₀)-alkyl, (C₃-C₁₀)-alkenyl or (C₃-C₁₀)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,        di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,        [(C₁-C₄)-haloalkoxy]-carbonyl,    -   (C₃-C₆)-cycloalkyl, which is unsubstituted or substituted by one        or more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl, preferably unsubstituted or        substituted by (C₁-C₄)-alkyl,    -   phenyl, which is unsubstituted or substituted by one or more        radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio, and    -   heterocyclyl, which is unsubstituted or substituted by one or        more radicals selected from the group consisting of halogen,        (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,        (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,-    or (C₃-C₆)-cycloalkyl or (C₃-C₆)-cycloalkyl which is condensed at    one side of the ring to a 4- to 6-membered saturated or unsaturated    carbocyclic ring,    -   where each of the 2 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of (C₁-C₄)-alkyl,-    preferably (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl,    -   where each of the 3 last mentioned radicals is unsubstituted or        substituted by one or more radicals selected from the group        consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,        (C₁-C₄)-alkylthio and (C₁-C₄)-alkoxycarbonyl,-    more preferably (C₁-C₆)-alkyl, (C₂-C₆)-alkenyl or (C₂-C₆)-alkynyl,    where each of the 3 last mentioned radicals is unsubstituted or    substituted by one or more radicals selected from the group    consisting of (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio    and (C₁-C₄)-alkoxycarbonyl,-   or-   R³ and R⁴ together with the directly attached nitrogen atom are a    four- to eight-membered heterocyclic ring, preferably a 5- or    6-membered heterocyclic ring, which, in addition to the nitrogen    atom, may also contain further hetero ring atoms, preferably up to    two further hetero ring atoms from the group consisting of N, O and    S, and which is unsubstituted or substituted by one or more radicals    selected from the group consisting of halogen, cyano, nitro,    (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy    and (C₁-C₄)-alkylthio,-   or-   R³ and R together with the directly attached nitrogen atom are the    group —N═CR⁵—NR⁶R⁷, in which-    R⁵ is hydrogen or (C₁-C₄)-alkyl, with hydrogen being preferred, and-    R⁶, R⁷ independently of one another are hydrogen or (C₁-C₄)-alkyl,    preferably (C₁-C₂)-alkyl, or R⁶ and R⁷ together with the directly    attached nitrogen atom form a five- or six-membered, preferably    saturated heterocyclic ring, such as, for example, piperidinyl,    pyrrolidinyl or morpholinyl.

Particular preference is also given to the use according to theinvention of compounds of the formula (I) or salts thereof in which

-   R¹ is a (C₁-C₆)-haloalkyl radical, preferably from the group    consisting of CF₃, CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁, CF₂CF₂CF₃    and C(CH₃)₂F, more preferably CF₃, CF₂C₁, CF₂H, CF₂CF₂CF₃ or CF₂CF₃,    even more preferably CF₃, CF₂C₁, CF₂CF₂CF₃ or CF₂CF₃, in particular    CF₃, CF₂CF₃ or CF₂Cl, and-   R² is halogen and-   R³ is hydrogen and-   R⁴ is hydrogen.

Likewise particularly preferred is the use according to the invention ofcompounds of the formula (I) or salts thereof in which

-   R¹ is CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H or CF₂CF₂Cl, more preferably    CF₂C₁ or CF₂H or CF₂CF₃, more preferably CF₂C₁ or CF₂CF₃, in    particular CF₂Cl,-   R² is hydrogen and-   R³ is hydrogen or (C₁-C₄)-alkyl and-   R⁴ is hydrogen.

Particular preference is also given to the use according to theinvention of compounds of the formula (I) or salts thereof in which thegeneral radicals correspond to the radicals mentioned for R¹, R², R³ andR⁴, respectively, in the examples given in the tables, or embrace them.

Particular preference is also given to the use according to theinvention of novel compounds of the formula (I) or salts thereof inwhich R¹, R², R³ and R⁴ furthermore preferably have the meaningsmentioned for the preferred uses.

The compounds of the general formula (I) can be prepared, for example,by

-   (a) reacting a carboxylic acid of the general formula (II)

-   -   in which R¹ and R² are as defined for the compound of the        formula (I) to be prepared,    -   with an amine of the formula (III) or a salt thereof,

-   -   in which R³ and R⁴ are as defined for the compound of the        formula (I) to be prepared,    -   if appropriate in the presence of a carboxylic acid-activating        reagent, for example N,N-carbonyldiimidazole (CDI), or a        dehydrating agent, for example dicyclohexylcarbodiimide (DCC),        to give the compound of the formula (I) or

-   (b) reacting a carboxylic ester of the general formula (IV)

-   -   in which R¹ and R² are as defined for the compound of the        formula (I) to be prepared and “Alkyl” is an alkyl radical, for        example methyl or ethyl, with an amine of the formula (III) or a        salt thereof,

-   -   in which R³ and R⁴ are as defined for the compound of the        formula (I) to be prepared, to give the compound of the        formula (I) or

-   (c) reacting a carbonyl halide or a carboxylic anhydride of the    general formula (V),

-   -   in which R¹ and R² are as defined for the compound of the        formula (I) to be prepared and Hal is a halogen atom, for        example chlorine, or an acyloxy radical, with an amine of the        formula (III) or a salt thereof,

-   -   in which R³ and R⁴ are as defined for the compound of the        formula (I) to be prepared, to give the compound of the formula        (I),

-   (d), if R³ and R⁴ in the compound of the formula (I) to be prepared    are each hydrogen,    -   reacting a compound of the formula (VI),

-   -   in which R¹ is as defined for the compound of the formula (I) to        be prepared, and “Alkyl” is an alkyl radical, for example methyl        or ethyl,    -   with malonamide to give the compound of the formula (I).

The amide formations according to variant (a) can be carried out, forexample, in an inert organic solvent in a temperature range between 0°C. and 150° C., preferably between 0° C. and 50° C. Suitable organicsolvents are, for example, polar protic or aprotic solvents, such asethers, for example diethyl ether, tetrahydrofuran and dioxane, ornitriles, such as acetonitrile, or amides, such as dimethylformamide.The amide formations according to variant (b) can be carried out, forexample, in an inert organic solvent in a temperature range between 0°C. and 150° C., preferably between 50° C. and 100° C. Suitable organicsolvents are, for example, polar protic or aprotic solvents, such asethers, for example tetrahydrofuran and dioxane, or nitriles, such asacetonitrile, or amides, such as dimethylformamide. However, preferenceis given to the amide formation according to variant (b) at elevatedtemperatures by reacting the undiluted reactants.

The amide formations according to variant (c) can be carried out, forexample, in the presence of an acid binder in an inert organic solventin a temperature range between 0° C. and 150° C., preferably between 50°C. and 100° C. Suitable organic solvents are, for example, polar proticor aprotic solvents, such as ethers, for example diethyl ether,tetrahydrofuran and dioxane, or nitriles, such as acetonitrile, oramides, such as dimethylformamide. Acid binders are, for example, alkalimetal or alkaline earth metal carbonates, such as, for example, sodiumcarbonate, potassium carbonate or calcium carbonate, alkali metal oralkaline earth metal hydroxides, such as sodium hydroxide, potassiumhydroxide or calcium hydroxide, or alkali metal hydrides or amides, suchas sodium hydride or potassium hydride or sodium amide or potassiumamide, or else organic bases, such as triethylamine, pyridine,dimethylaminopyridine, DBU (1,8-diazabicyclo[5.4.0]-undec-7-ene), DBN(1,5-diazabicyclo[4.3.0]non-5-ene) and 1,4-diaza-bicyclo[2.2.2]octane.

The amide formations according to variant (d) can be carried outanalogously to the processes described in EP 522392 and Helv. Chim. Acta71 (1988) 596-601 and GB 2305174. In general, the malonamide can beconverted in an organic anhydrous polar protic or aprotic solvent, forexample in an alcohol, with a strong base, such as an alkali metal,alkali metal hydride or alkali metal alkoxide, into a reactive salt, andthen be reacted with the compound of the formula (VI). The reaction withthe compound (VI) can generally be carried out in a temperature rangebetween 0° C. and the boiling point of the solvent (depending on thesolvent up to about 150° C.).

The compounds of the general formulae (II), (III), (IV) and (V) areeither commercially available or can be prepared by or analogously tomethods known to the person skilled in the art (for example Helv. Chim.Acta 71 (1988) 596; EP 502740 (U.S. Pat. No. 5,393,734); EP 522392).

Thus, for example, the compounds of the formula (IVa)

can be obtained by reacting alkoxyvinyl ethers of the formula (VI) withalkyl malonamides of the formula (VII).

The starting materials of the formula (VI) are either commerciallyavailable or can be prepared by known methods (for example Synthesis2000, 738-742; J. Fluor. Chem., 107, 2001, 285-300; Organometallics 15,1996, 5374-5379).

The compounds of the formula (IV) in which R² is a halogen atom can beprepared by customary halogenations from the compounds of the formula(IVa). Suitable for use as halogenating agents for pyridine are, forexample, chlorine (J. Org. Chem. 23, 1958, 1614), bromine (Synth.Commun. 19, 1989, 553-560; U.S. Pat. No. 2,532,055), iodine (TetrahedronLett. 45, 2004, 6633-6636), sodium hypochlorite (J. Org. Chem. 49, 1984,4784-4786; J. Med. Chem. 36, 1993, 2676-2688, U.S. Pat. No. 4,960,896),sodium hypobromite (J. Med. Chem. 32, 1989, 2178-2199), thionyl chloride(Organic Letters, 6, 2004, 3-5), N-chlorosuccinimide (J. Med. Chem. 46,2003, 702-715), N-bromosuccinimide (Chem. Pharm. Bull. 48, 2000,1847-1853), N-iodosuccinimide (J. Med. Chem. 36, 1993, 2676-2788).

Furthermore, the compounds of the formula (IV) can be prepared from thecompounds of the formula (IVa) by successive nitration (for example J.Med. Chem. 36, 1993, 2676-2688; J. Heterocycl. Chem. 33, 1996, 287-294),reduction (for example J. Med. Chem. 33, 1990, 1859-1865), diazotationand subsequent reaction of the diazonium salts in a Sandmeyer orSchiemann reaction.

The compounds of the formula (I) in which R³ and R⁴ together with thedirectly attached nitrogen atom are the group —N═CR⁵—NR⁶R⁷ can beprepared by reacting a compound of the formula (I) in which R³ and R⁴are hydrogen with compounds of the formula (VIII) in which R⁵, R⁶ and R⁷are as defined above

according to known methods (see, for example Synthesis 1980, 119-121; J.Med. Chem., 33, 1990, 2052-2059).

The invention also provides a method for protecting crop plants oruseful plants against phytotoxic actions of agrochemicals, such aspesticides or, in particular, herbicides which cause damage to cropplants or useful plants, which method comprises using compounds of theformula (I) or salts thereof as safeners, preferably by applying aneffective amount of the compounds of the formula (I) or salts thereof tothe plants, to parts of plants or their seeds (or seed).

The compounds (I) (=safeners), together with active compounds(pesticides), are suitable for use in the selective control of harmfulorganisms in a number of plant crops, for example in crops of economicimportance, such as cereals (wheat, barley, triticale, rye, rice, corn,millet), sugar beet, sugar cane, oilseed rape, cotton, sunflower, peas,beans and soybeans. Of particular interest is the use inmonocotyledonous crops, such as cereals (wheat, barley, rye, triticale,sorghum), including corn and rice, and monocotyledonous vegetable crops,but also in dicotyledonous crops, such as, for example, soybean, oilseedrape, cotton, grape vines, vegetable plants, fruit plants and ornamentalplants. The herbicide/safener combinations with the safeners (I) arealso suitable for controlling harmful plants in beds and plots of usefulplants and ornamental plants, such as, for example, lawn plots withuseful or ornamental lawn, especially lolium, meadow grass or Bermudagrass.

Also of interest from among the useful plants and crop plants in whichthe herbicide/safener combinations with safeners (I) may be used aremutant crops which are completely or partially tolerant to certainpesticides or completely or partially tolerant transgenic crops, forexample corn crops which are resistant to glufosinate or glyphosate, orsoybean crops which are resistant to herbicidal imidazolinones. However,the particular advantage of the safeners used in this novel way is theirefficient action in crops which normally are insufficiently tolerant tothe pesticides being applied.

For the joint use with pesticides, the compounds of the formula (I)according to the invention can be applied simultaneously with the activecompounds or in any order, and they are then capable of reducing orcompletely eliminating harmful side effects of these active compounds incrop plants, without negatively affecting or substantially reducing theactivity of these active compounds against unwanted harmful organisms.Here, even damage caused by using a plurality of pesticides, for examplea plurality of herbicides or herbicides in combination with insecticidesor fungicides, can be reduced substantially or eliminated completely. Inthis manner, it is possible to extend the field of use of conventionalpesticides considerably.

If the compositions according to the invention comprise pesticides,these compositions are, after appropriate dilution, applied eitherdirectly to the area under cultivation, to the already germinatedharmful and/or useful plants or to the already emerged harmful and/oruseful plants. If the compositions according to the invention do notcomprise any pesticide, these compositions can be employed by the tankmix method—i.e. the user mixes and dilutes the separately availableproducts (=the pesticide and the agent protecting the useful plants)immediately prior to application to the area to be treated—or prior tothe application of a pesticide, or after the application of a pesticide,or for the pretreatment of seed, i.e., for example, for dressing theseed of the useful plants. Preferably, safener and pesticide are appliedwithin a short time of one another, in particular when the safener isapplied to the plants after the herbicide.

The advantageous actions of the compounds (I) according to the inventionare observed when they are used together with the pesticides by thepre-emergence method or the post-emergence method, for example in thecase of simultaneous application as a tank mix or a coformulation or inthe case of a separate application, in parallel or in succession (splitapplication). It is also possible to repeat the application a number oftimes. In some cases, it may be expedient to combine a pre-emergenceapplication with a post-emergence application. In most cases, one optionis a post-emergence application to the useful plant or crop planttogether with a simultaneous or later application of the pesticide. Alsopossible is the use of the compounds (I) according to the invention forseed dressing, for (dip) treatment of seedlings (for example rice) orfor the treatment of other propagation material (for example potatotubers).

When using the compounds (I) according to the invention in combinationwith herbicides, in addition to the safener action, enhanced action, inthe herbicidal action, against harmful plants is frequently alsoobserved. Furthermore, in many cases, there is an improved growth of theuseful plants and crop plants, and it is possible to increase theharvest yields.

The compositions according to the invention may comprise one or morepesticides. Suitable pesticides are, for example, herbicides,insecticides, fungicides, acaricides and nematicides, which, when usedon their own, would cause phytotoxic damage to the crop plants or wouldprobably cause damage. Of particular interest are correspondingpesticidally active compounds from the groups of the herbicides,insecticides, acaricides, nematicides and fungicides, in particularherbicides.

The weight ratio of safener to pesticide can be varied within widelimits and is generally in the range from 1:100 to 100:1, preferablyfrom 1:20 to 20:1, in particular from 1:10 to 10:1. The optimum weightratio of safener to pesticide depends both on the respective safenerused and the respective pesticide, and on the type of useful plant orcrop plant to be protected. The required application rate of safenercan, depending on the pesticide used and the type of useful plant to beprotected, be varied within wide limits and is generally in the rangefrom 0.001 to 10 kg, preferably from 0.01 to 1 kg, in particular from0.05 to 0.5 kg, of safener per hectare. The weight ratios and amountsrequired for a successful treatment can be determined by simplepreliminary experiments.

For seed dressing, for example, from 0.005 to 20 g of safener perkilogram of seed, preferably from 0.01 to 10 g of safener per kilogramof seed, in particular from 0.05 to 5 g of safener per kilogram of seed,are used.

If solutions of safener are used for seed treatment and the seeds orseedlings are wetted with the solutions, the suitable concentration isgenerally in the range from 1 to 10 000 ppm, preferably from 100 to 1000ppm, based on the weight. The weight ratios and amounts required for asuccessful treatment can be determined by simple preliminaryexperiments.

The safeners can be formulated in the customary manner, separately ortogether with the pesticides. Accordingly, the present invention alsoprovides the useful-plant-protecting or crop-plant-protectingcompositions.

Preferred is the joint application of safener and pesticide, inparticular that of safener and herbicide as a readymix or the use by thetankmix method.

Preference is also given to using the safener (I) in the treatment ofseed, followed by the application of pesticides, preferably herbicides,after sowing by the pre- or post-emergence method.

The compounds of the formula (I) or their salts, as such or in the formof their preparations (formulations), can be used in combination withother pesticidally active compounds, such as, for example, insecticides,acaricides, nematicides, herbicides, fungicides, safeners, fertilizersand/or growth regulators, for example as finished formulation or as tankmixes. Here, the combination formulations can be prepared based on theformulations mentioned above, taking into account the physicalproperties and stabilities of the active compounds to be combined.Suitable as combination partners for the active compounds according tothe invention in formulations of mixtures or in tank-mixes are, forexample, known, preferably herbicidally active compounds whose action isbased on the inhibition of, for example, acetolactate synthase,acetyl-coenzyme-A carboxylase, PS I, PS II, HPPDO, phytoene desaturase,protoporphyrinogen oxidase, glutamine synthetase, cellulosebiosynthesis, 5-enolpyruvylshikimate 3-phosphate synthetase. Suchcompounds and also other compounds which can be used, in some caseshaving an unknown or a different mechanism of action, are described, forexample, in Weed Research 26, 441-445 (1986), or in “The PesticideManual”, 12th edition 2000, or 13th edition 2003 or 14h edition2006/2007, or in the corresponding “e-Pesticide Manual”, version 4(2006), all published by the British Crop Protection Council,(hereinbelow also referred to in short as “PM”), and in the literaturecited therein. Lists of “common names” are also available in “TheCompendium of Pesticide Common Names” on the Internet. Examples ofherbicides known from the literature which may be combined with thecompounds of the formula (I) are, for example, the following activecompounds (note: the compounds are referred to either by the “commonname” according to the International Organization for Standardization(ISO) or by the chemical name, if appropriate together with a customarycode number):

acetochlor; acibenzolar-5-methyl; acifluorfen(-sodium); aclonifen;AD-67; AKH 7088, i.e.[[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]-amino]oxy]aceticacid and methyl[[[1-[5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrophenyl]-2-methoxyethylidene]amino]oxy]acetate;alachlor; alloxydim(-sodium); ametryn; amicarbazone, amidochlor,amidosulfuron; aminopyralid; amitrol; AMS, i.e. ammonium sulfamate;ancimidol; anilofos; asulam; atrazine; aviglycine; azafenidin,azimsulfuron (DPX-A8947); aziprotryn; barban; BAS 516H, i.e.5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamid (UBH-509),benazolin(-ethyl); bencarbazone; benfluralin; benfuresate; benoxacor;bensulfuron(-methyl); bensulide; bentazone; benzfendizone;benzobicyclon, benzofenap; benzofluor; benzoylprop(-ethyl);benzthiazuron; bialaphos; bifenox; bispyribac(-sodium) (KIH-2023);borax; bromacil; bromobutide; bromofenoxim; bromoxynil; bromuron;buminafos; busoxinone; butachlor; butafenacil, butamifos; butenachlor(KH-218); buthidazole; butralin; butroxydim, butylate; cafenstrole(CH-900); carbetamide; carfentrazone(-ethyl); CDM, i.e.2-chloro-N,N-di-2-propenylacetamide; CDEC, i.e. 2-chlorallyldiethyldithiocarbamate; chlomethoxyfen; chloramben; chlorazifop-butyl,chlorbromuron; chlorbufam; chlorfenac; chlorfenprop;chlorflurecol(-methyl); chlorflurenol(-methyl); chloridazon;chlorimuron(-ethyl); chlormequat(chloride); chlornitrofen; chlorphthalim(MK-616); chlorotoluron; chloroxuron; chlorpropham; chlorsulfuron;chlorthal-dimethyl; chlorthiamid; chlortoluron, cinidon(-methyl and-ethyl), cinmethylin; cinosulfuron; clefoxydim, clethodim; clodinafopand its ester derivatives (for example clodinafop-propargyl); clofencet;clomazone; clomeprop; cloprop; cloproxydim; clopyralid;clopyrasulfuron(-methyl), cloquintocet(-mexyl); cloransulam(-methyl),cumyluron (JC 940); cyanamide; cyanazine; cycloate; cyclosulfamuron (AC104); cycloxydim; cycluron; cyhalofop and its ester derivatives (forexample the butyl ester, DEH-112); cyperquat; cyprazine; cyprazole;cyprosulfamide; daimuron; 2,4-D, 2,4-DB; dalapon; daminozide; dazomet;n-decanol; desmedipham; desmetryn; di-allate; dicamba; dichlobenil;dichlormid; dichlorprop(-P) salts; diclofop and its esters, such asdiclofop-methyl; diclofop-P(-methyl); diclosulam, diethatyl(-ethyl);difenoxuron; difenzoquat(metilsulfate); diflufenican;diflufenzopyr(-sodium); dimefuron; dimepiperate, dimethachlor;dimethametryn; dimethazone; dimethenamid (SAN-582H); dimethenamide-P;dimethylarsinic acid; dimethipin; dimetrasulfuron, dinitramine; dinoseb;dinoterb; diphenamid; dipropetryn; diquat salts; dithiopyr; diuron;DNOC; eglinazine-ethyl; EL 77, i.e.5-cyano-1-(1,1-dimethylethyl)-N-methyl-1H-pyrazole-4-carboxamide;endothal; epoprodan, EPTC; esprocarb; ethalfluralin;ethametsulfuron-methyl; ethephon; ethidimuron; ethiozin; ethofumesate;ethoxyfen and its esters (for example the ethyl ester, HN-252);ethoxysulfuron, etobenzanid (HW 52); F5231, i.e.N-[2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl]-ethanesulfonamide;fenchlorazole(-ethyl); fenclorim; fenoprop; fenoxan, fenoxaprop andfenoxaprop-P and also their esters, for example fenoxaprop-P-ethyl andfenoxaprop-ethyl; fenoxydim; fentrazamide, fenuron; ferrous sulfate;flamprop(-methyl or -isopropyl or -isopropyl-L); flamprop-M(-methyl or-isopropyl); flazasulfuron; florasulam, fluazifop and fluazifop-P andtheir esters, for example fluazifop-butyl and fluazifop-P-butyl;fluazolate, flucarbazone(-sodium), flucetosulfuron; fluchloralin;flufenacet; flufenpyr(-ethyl); flumetralin; flumetsulam; flumeturon;flumiclorac(-pentyl), flumioxazin (S-482); flumipropyn; fluometuron,fluorochloridone, fluorodifen; fluoroglycofen(-ethyl); flupoxam(KNW-739); flupropacil (UBIC-4243); flupropanoate;flupyrsulfuron(-methyl)(-sodium); flurazole; flurenol(-butyl);fluridone; fluorochloridone; fluoroxypyr(-meptyl); flurprimidol,flurtamone; fluthiacet(-methyl) (KIH-9201); fluthiamide, fluxofenim;fomesafen; foramsulfuron, forchlorfenuron; fosamine; furilazole;furyloxyfen; gibberillic acid; glufosinate(-ammonium);glyphosate(-isopropylammonium); halosafen; halosulfuron(-methyl);haloxyfop and its esters; haloxyfop-P (=R-haloxyfop) and its esters;HC-252; hexazinone; imazamethabenz(-methyl); imazamethapyr, imazamox,imazapic, imazapyr; imazaquin and salts, such as the ammonium salt;imazethamethapyr; imazethapyr; imazosulfuron; inabenfide; indanofan;indole-3-acetic acid; 4-indol-3-ylbutyric acid;iodosulfuron-methyl(-sodium); ioxynil; isocarbamid; isopropalin;isoproturon; isouron; isoxaben; isoxachlortole, isoxadifen(-ethyl);isoxaflutole, isoxapyrifop; karbutilate; lactofen; lenacil; linuron;maleic hydrazide (MH), MCPA; MCPB; mecoprop(-P); mefenacet;mefenpyr(-diethyl); mefluidid; mepiquat(-chloride);mesosulfuron(-methyl); mesotrione, metam; metamifop; metamitron;metazachlor; methabenzthiazuron; metham; methazole; methoxyphenone;methylarsonic acid; methylcyclopropene; methyldymron; methylisothiocyanate; methabenzthiazuron; metobenzuron; metobromuron;(alpha-)-metolachlor; metosulam (XRD 511); metoxuron; metribuzin;metsulfuron-methyl; molinate; monalide; monocarbamide dihydrogensulfate;monolinuron; monuron; MT 128, i.e.6-chloro-N-(3-chloro-2-propenyl)-5-methyl-N-phenyl-3-pyridazinamine; MT5950, i.e. N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide;naproanilide; napropamide; naptalam; NC 310, i.e.4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole; neburon;nicosulfuron; nipyraclofen; nitralin; nitrofen; nitrophenolate mixture;nitrofluorfen; nonanoic acid; norflurazon; orbencarb; orthasulfamuron;oxabetrinil; oryzalin; oxadiargyl (RP-020630); oxadiazon; oxasulfuron,oxaziclomefone, oxyfluorfen; paclobutrazol; paraquat(dichloride);pebulate; pelargonic acid, pendimethalin; penoxsulam; pentachlorophenol;pentanochlor; pentoxazone, perfluidone; pethoxamid; phenisopham;phenmedipham; picloram; picolinafen, pinoxaden, piperophos;piributicarb; pirifenop-butyl; pretilachlor; primisulfuron(-methyl);probenazole; procarbazone-(sodium), procyazine; prodiamine; profluralin;profoxydim; prohexadione(-calcium); prohydrojasmon;proglinazine(-ethyl); prometon; prometryn; propachlor; propanil;propaquizafop; propazine; propham; propisochlor;propoxycarbazone(-sodium) (MKH-6561); n-propyl dihydrojasmonate;propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005);prynachlor; pyraclonil; pyraflufen(-ethyl) (ET-751); pyrasulfotole;pyrazolynate; pyrazon; pyrazosulfuron(-ethyl); pyrazoxyfen;pyribenzoxim, pyributicarb, pyridafol, pyridate; pyriftalid;pyriminobac(-methyl) (KIH-6127); pyrimisulfan (KIH-5996);pyrithiobac(-sodium) (KIH-2031); pyroxasulfone (KIH-485); pyroxofop andits esters (for example the propargyl ester); pyroxsulam; quinclorac;quinmerac; quinoclamine, quinofop and its ester derivatives, quizalofopand quizalofop-P and their ester derivatives, for examplequizalofop-ethyl; quizalofop-P-tefuryl and -ethyl; renriduron;rimsulfuron (DPX-E 9636); S 275, i.e.2-[4-chloro-2-fluoro-5-(2-propynyloxy)phenyl]-4,5,6,7-tetrahydro-2H-indazol;saflufenacil(N′-[2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydro-1(2H)-pyrimidinyl)benzoyl]-N-isopropyl-N-methylsulfamide),secbumeton; sethoxydim; siduron; simazine; simetryn; sintofen; SN106279, i.e.2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoicacid and methyl2-[[7-[2-chloro-4-(trifluoromethyl)phenoxy]-2-naphthalenyl]oxy]propanoate;sulcotrione, sulfentrazone (FMC-97285, F-6285); sulfazuron;sulfometuron(-methyl); sulfosate (ICI-A0224); sulfosulfuron, TCA;tebutam (GCP-5544); tebuthiuron; tecnacene; tembotrione; tefuryltrione;tepraloxydim, terbacil; terbucarb; terbuchlor; terbumeton;terbuthylazine; terbutryn; TFH 450, i.e.N,N-diethyl-3-[(2-ethyl-6-methylphenyl)sulfonyl]-1H-1,2,4-triazole-1-carboxamide;thenylchlor (NSK-850); thiafluamide, thiazafluoron; thiazopyr(Mon-13200); thidiazimin (SN-24085); thidiazuron; thiencarbazone;thifensulfuron(-methyl); thiobencarb; Ti 35; tiocarbazil; topramezone;tralkoxydim; tri-allate; triasulfuron; triaziflam, triazofenamide;tribenuron(-methyl); triclopyr; tridiphane; trietazine;trifloxysulfuron; trifluralin; triflusulfuron and esters (for examplethe methyl ester, DPX-66037); trimeturon; trinexapac; tritosulfuron,tsitodef; uniconazole; vernolate; WL 110547, i.e.5-phenoxy-1-[3-(trifluoromethyl)phenyl]-1H-tetrazole; D-489; LS 82-556;KPP-300; NC-324; NC-330; DPX-N8189; SC-0774; DOWCO-535; DK-8910;V-53482; PP-600 and MBH-001.

Insecticides which may cause damage to plants when used on their own ortogether with herbicides are, for example, the following:

Organophosphates, for example terbufos (Counter®), fonofos (Dyfonate®),phorate (Thimet®), chlorpyriphos (Reldan®), carbamates, such ascarbofuran (Furadan®), pyrethroid insecticides, such as tefluthrin(Force®), deltamethrin (Decis®) and tralomethrin (Scout®), and otherinsecticidal agents having a different mechanism of action.

Herbicides, whose phytotoxic side effects on crop plants can be reducedusing compounds of the formula (I) are, for example, herbicides from thegroup of the carbamates, thiocarbamates, haloacetanilides, substitutedphenoxy-, naphthoxy- and phenoxyphenoxycarboxylic acid derivatives andheteroaryloxyphenoxyalkane-carboxylic acid derivatives, such asquinolyloxy-, quinoxalyloxy-, pyridyloxy-, benzoxazolyloxy- andbenzothiazolyloxyphenoxyalkanecarboxylic acid esters, cyclo-hexanedioneoximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoyl-pyrazoles,imidazolinones, pyrimidinyloxypyridinecarboxylic acid derivatives,pyrimidyloxybenzoic acid derivatives, sulfonylureas,sulfonylaminocarbonyl-triazolinones, triazolopyrimidinesulfonamidederivatives, phosphinic acid derivatives and salts thereof, glycinederivatives, triazolinones, triazinones and alsoS-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphoric esters,pyridinecarboxylic acids, pyridines, pyridinecarboxamides,1,3,5-triazines and others.

Preference is given here to phenoxyphenoxy- andheteroaryloxyphenoxycarboxylic acid esters and salts, cyclohexanedioneoximes, benzoylcyclohexanediones, benzoylisoxazoles, benzoylpyrazolessulfonylureas, sulfonylaminocarbonyltriazolinones, imidazolinones andmixtures of the active compounds mentioned with one another and/or withactive compounds used for broadening the activity spectrum of theherbicides, for example bentazone, cyanazine, atrazine, bromoxynil,dicamba and other leaf-acting herbicides.

Herbicides which are suitable for combination with the safenersaccording to the invention are, for example:

A) herbicides of the type of the phenoxyphenoxy- andheteroaryloxyphenoxy-carboxylic acid derivatives, such as

-   A1) phenoxyphenoxy- and benzyloxyphenoxycarboxylic acid derivatives,    for example methyl 2-(4-(2,4-dichlorophenoxy)phenoxy)propionate    (diclofop-methyl), methyl    2-(4-(4-bromo-2-chlorophenoxy)phenoxy)propionate (DE-A 26 01 548    (U.S. Pat. No. 4,370,489)),-   methyl 2-(4-(4-bromo-2-fluorophenoxy)phenoxy)propionate (U.S. Pat.    No. 4,808,750),-   methyl 2-(4-(2-chloro-4-trifluoromethylphenoxy)phenoxy)propionate    (DE-A 24 33 067 (U.S. Pat. No. 4,332,960)),-   methyl 2-(4-(2-fluoro-4-trifluoromethylphenoxy)phenoxy)propionate    (U.S. Pat. No. 4,808,750),-   methyl 2-(4-(2,4-dichlorobenzyl)phenoxy)propionate (DE-A 24 17 487    (U.S. Pat. No. 4,088,474)),-   ethyl 4-(4-(4-trifluoromethylphenoxy)phenoxy)pent-2-enoate,-   methyl 2-(4-(4-trifluoromethylphenoxy)phenoxy)propionate (DE-A 24 33    067),-   butyl (R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionate    (cyhalofop-butyl)-   A2) “monocyclic” heteroaryloxyphenoxyalkanecarboxylic acid    derivatives, for example-   ethyl 2-(4-(3,5-dichloropyridyl-2-oxy)phenoxy)propionate (EP-A 0 002    925),-   propargyl 2-(4-(3,5-dichloropyridyl-2-oxy)phenoxy)propionate (EP-A 0    003 114 (U.S. Pat. No. 4,300,944)),-   methyl (RS)- or    (R)-2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate    (haloxyfop-methyl or haloxyfop-P-methyl),-   ethyl    2-(4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate    (EP-A 0 003 890 (U.S. Pat. No. 4,840,664)),-   propargyl 2-(4-(5-chloro-3-fluoro-2-pyridyloxy)phenoxy)propionate    (clodinafop-propargyl),-   butyl (RS)- or    (R)-2-(4-(5-trifluoromethyl-2-pyridyloxy)phenoxy)propionate    (fluazifop-butyl or fluazifop-P-butyl),-   (R)-2-[4-(3-chloro-5-trifluoromethyl-2-pyridyloxy)phenoxy]propionic    acid-   A3) “bicyclic” heteroaryloxyphenoxyalkanecarboxylic acid    derivatives, for example-   methyl and ethyl (RS)- or    (R)-2-(4-(6-chloro-2-quinoxalyloxy)phenoxy)propionate    (quizalofop-methyl and -ethyl or quizalofop-P-methyl and -P-ethyl),-   methyl 2-(4-(6-fluoro-2-quinoxalyloxy)phenoxy)propionate (see J.    Pest. Sci. Vol. 10, 61 (1985)),-   2-isopropylidenaminooxyethyl    (R)-2-(4-(6-chloro-2-quinoxalyloxy)phenoxy)propionate    (propaquizafop),-   ethyl (RS)- or    (R)-2-(4-(6-chlorobenzoxazole-2-yloxy)phenoxy)propionate    (fenoxaprop-ethyl or fenoxaprop-P-ethyl),-   ethyl 2-(4-(6-chlorobenzothiazol-2-yloxy)phenoxy)propionate (DE-A-26    40 730 (U.S. Pat. No. 4,130,413)),-   tetrahydro-2-furylmethyl (RS)- or    (R)-2-(4-(6-chloroquinoxalyloxy)phenoxy) propionate (EP-A-0 323 727    (U.S. Pat. No. 5,120,348));-   (R)-2-[4-(6-chloro-1,3-benzoxazol-2-yloxy)phenoxy]-2′-fluoro-N-methylpropionanilide    (metamifop);    B) herbicides from the group of the sulfonylureas, such as    pyrimidinyl- or triazinylaminocarbonyl[benzene-, -pyridine-,    -pyrazole-, -thiophene- and -(alkyl-sulfonyl)alkylamino]sulfamides.    Preferred substituents on the pyrimidine ring or the triazine ring    are alkoxy, alkyl, haloalkoxy, haloalkyl, halogen or dimethylamino,    it being possible to combine all substituents independently of one    another. Preferred substituents in the benzene, pyridine, pyrazole,    thiophene or (alkylsulfonyl)alkyl-amino moiety are alkyl, alkoxy,    halogen, nitro, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,    dialkylaminocarbonyl, alkoxyaminocarbonyl, haloalkoxy, haloalkyl,    alkylcarbonyl, alkoxyalkyl, (alkanesulfonyl)alkylamino. Such    suitable sulfonylureas are, for example,-   B1) phenyl- and benzylsulfonylureas and related compounds, for    example-   1-(2-chlorophenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea    (chlorsulfuron),-   1-(2-ethoxycarbonylphenysulfonyl)-3-(4-chloro-6-methoxypyrimidin-2-yl)urea    (chlorimuron-ethyl),-   1-(2-methoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea    (metsulfuron-methyl),-   1-(2-chloroethoxyphenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea    (triasulfuron),-   1-(2-methoxycarbonylphenylsulfonyl)-3-(4,6-dimethylpyrimidin-2-yl)urea    (sulfumeturon-methyl),-   1-(2-methoxycarbonylphenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-methylurea    (tribenuron-methyl),-   1-(2-methoxycarbonylbenzylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea    (bensulfuron-methyl),-   1-(2-methoxycarbonylphenylsulfonyl)-3-(4,6-bis-(difluoromethoxy)pyrimidin-2-yl)urea    (primisulfuron-methyl),-   3-(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]-thiophene-7-sulfonyl)urea    (EP-A 0 079 683 (U.S. Pat. No. 4,492,596),-   3-(4-ethoxy-6-ethyl-1,3,5-triazin-2-yl)-1-(2,3-dihydro-1,1-dioxo-2-methylbenzo[b]-thiophene-7-sulfonyl)urea    (EP-A 0 079 683),-   3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-1-(2-methoxycarbonyl-5-iodophenyl-sulfonyl)urea    (WO 92/13845 (U.S. Pat. No. 5,463,081)),-   methyl    2-[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-ylcarbamoyl-sulfamoyl]-3-methylbenzoate    (DPX-66037, triflusulfuron-methyl),-   oxetan-3-yl    2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate    (CGA-277476, oxasulfuron),-   methyl    4-iodo-2-[3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureidosulfonyl]benzoate,    sodium salt (iodosulfuron-methyl-sodium),-   methyl    2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-methanesulfonylamino-methylbenzoate    (mesosulfuron-methyl, WO 95/10507 (U.S. Pat. No. 5,648,315)),-   N,N-dimethyl-2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-4-formylamino-benzamide    (foramsulfuron, WO 95/01344 (U.S. Pat. No. 5,658,854)),-   1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenylsulfonyl]urea    (cinosulfuron),-   methyl    2-[(4-ethoxy-6-methylamino-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoate    (ethametsulfuron-methyl),-   1-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(3,3,3-trifluoropropyl)phenylsulfonyl]-urea    (prosulfuron),-   1-(4-methoxy-6-trifluoromethyl-1,3,5-triazin-2-yl)-3-(2-trifluoromethyl-benzenesulfonyl)urea    (tritosulfuron);-   N-[(4-methylpyrimidin-2-yl)carbamoyl]-2-nitrobenzenesulfonamide    (monosulfuron),-   methyl-2-[({[4-methoxy-6-(methylthio)pyrimidin-2-yl]carbamoyl}amino)sulfonyl]-benzoate-   B2) thienylsulfonylureas, for example-   1-(2-methoxycarbonylthiophen-3-yl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea    (thifensulfuron-methyl);-   B3) pyrazolylsulfonylureas, for example-   1-(4-ethoxycarbonyl-1-methylpyrazol-5-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)-urea    (pyrazosulfuron-ethyl),-   methyl    3-chloro-5-(4,6-dimethoxypyrimidin-2-ylcarbamoylsulfamoyl)-1-methyl-pyrazole-4-carboxylate    (halosulfuron-methyl),-   methyl    5-(4,6-dimethylpyrimidin-2-yl-carbamoylsulfamoyl)-1-(2-pyridyl)pyrazole-4-carboxylate    (NC-330, see Brighton Crop Prot. Conference ‘Weeds’ 1991, Vol. 1, p.    45 et seq.),-   1-(4,6-dimethoxypyrimidin-2-yl)-3-[1-methyl-4-(2-methyl-2H-tetrazol-5-yl)pyrazol-5-yl-sulfonyl]urea    (DPX-A8947, azimsulfuron);-   N-[(4,6-dimethoxypyrimid    in-2-yl)carbamoyl]-4-(5,5-dimethyl-4,5-dihydroisoxazol-3-yl)-1,3-dimethyl-1H-pyrazole-5-sulfonamide;-   B4) sulfonediamide derivatives, for example-   3-(4,6-dimethoxypyrimidin-2-yl)-1-(N-methyl-N-methylsulfonylaminosulfonyl)urea    (amidosulfuron) and its structural analogs (EP-A 0 131 258 (U.S.    Pat. No. 4,601,747) and Z. Pfl. Krankh. Pfl. Schutz, special issue    XII, 489-497 (1990));-   B5) pyridylsulfonylureas, for example-   1-(3-N,N-dimethylaminocarbonylpyridin-2-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)-urea    (nicosulfuron),-   1-(3-ethylsulfonylpyridin-2-ysulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea    (rimsulfuron),-   methyl    2-[3-(4,6-dimethoxypyrimidin-2-yl)ureidosulfonyl]-6-trifluoromethyl-3-pyridine-carboxylate,    sodium salt (DPX-KE 459, flupyrsulfuron-methyl-sodium),-   3-(4,6-dimethoxypyrimidin-2-yl)-1-(3-N-methylsulfonyl-N-methylaminopyridin-2-yl)-sulfonylurea    or its salts (DE-A 40 00 503 (U.S. Pat. No. 5,494,886) and DE-A 40    30 577),-   1-(4,6-dimethoxypyrimidin-2-yl)-3-(3-trifluoromethyl-2-pyridylsulfonyl)urea    (flazasulfuron),-   1-(4,6-dimethoxypyrimidin-2-yl)-3-[3-(2,2,2-trifluoroethoxy)-2-pyridylsulfonyl]urea    sodium salt (trifloxysulfuron-sodium);-   (1RS,2RS;    1RS,2SR)-1-{3-[(4,6-dimethoxypyrimidin-2-ylcarbamoyl)sulfamoyl]-2-pyridyl}-2-fluoropropyl    methoxyacetate (flucetosulfuron);-   B6) alkoxyphenoxysulfonylureas, for example-   3-(4,6-dimethoxypyrimidin-2-yl)-1-(2-ethoxyphenoxy)sulfonylurea or    its salts (ethoxy-sulfuron);-   B7) imidazolylsulfonylureas, for example-   1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonyl-urea    (MON 37500, sulfosulfuron),-   1-(2-chloroimidazo[1,2-a]pyridin-3-ylsulfonyl)-3-(4,6-dimethoxypyrimidin-2-yl)urea    (imazosulfuron);-   2-chloro-N-[(4,6-dimethoxypyrimidin-2-yl)carbamoyl]-6-propylimidazo[1,2-b]pyridazine-3-sulfonamide;-   B8) phenylaminosulfonylureas, for example-   1-[2-(cyclopropylcarbonyl)phenylaminosulfonyl]-3-(4,6-dimethoxypyrimidin-2-yl)urea    (cyclosulfamuron);-   1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylcarbamoyl)phenylsulfamoyl]urea    (orthosulfamuron);-   C) chloroacetanilides, for example-   acetochlor, alachlor, butachlor, dimethachlor, dimethenamid,    dimethenamid-P; metazachlor,-   metolachlor, S-metolachlor, pethoxamid, pretilachlor, propachlor,    propisochlor and thenylchlor;-   D) thiocarbamates, for example-   S-ethyl N,N-dipropylthiocarbamate (EPTC),-   S-ethyl N,N-diisobutylthiocarbamate (butylate);-   cycloate, dimepiperate, esprocarb, molinate, orbencarb, pebulate,    prosulfocarb, thiobencarb, tiocarbazil, tri-allate and vernolate;-   E) cyclohexanedione oximes, for example-   alloxydim, butroxydim, clethodim, cloproxydim, cycloxydim,    profoxydim, sethoxydim, tepraloxydim and tralkoxydim;-   F) imidazolinones, for example-   imazamethabenz-methyl, imazapic, imazamox, imazapyr, imazaquin and    imazethapyr;-   G) triazolopyrimidinesulfonamide derivatives, for example-   chloransulam-methyl, diclosulam, florasulam, flumetsulam, metosulam    and penoxsulam, i.e.    2-(2,2-difluoroethoxy)-N-(5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-yl)-6-(trifluoromethyl)benzenesulfonamide,    and pyroxsulam, i.e.    N-(5,7-dimethoxy[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)-3-pyridinesulfonamide;-   H) benzoylcyclohexanediones, for example-   2-(2-chloro-4-methylsulfonylbenzoyl)cyclohexane-1,3-dione (SC-0051,    sulcotrione),-   2-(2-nitrobenzoyl)-4,4-dimethylcyclohexane-1,3-dione (EP-A 0 274    634),-   2-(2-nitro-3-methylsulfonylbenzoyl)-4,4-dimethylcyclohexane-1,3-dione    (WO 91/13548),-   2-[4-(methylsulfonyl)-2-nitrobenzoyl]-1,3-cyclohexanedione    (mesotrione)-   2-[2-chloro-3-(5-cyanomethyl-4,5-dihydroisoxazol-3-yl)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-(5-cyanomethyl-4,5-dihydroisoxazol-3-yl)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-(5-ethoxymethyl-4,5-dihydroisoxazol-3-yl)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-(5-ethoxymethyl-4,5-dihydroisoxazol-3-yl)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-[(2,2,2-trifluoroethoxy)methyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-[(2,2-trifluoroethoxy)methyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione    (tembotrione),-   2-[2-chloro-3-[(2,2-difluoroethoxy)methyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-[(2,2-difluoroethoxy)methyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-[(2,2,3,3-tetrafluoropropoxy)methyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-[(2,2,3,3-tetrafluoropropoxy)methyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-(cyclopropylmethoxy)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-(cyclopropylmethoxy)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-(tetrahydrofuran-2-ylmethoxymethyl)-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-(tetrahydrofuran-2-ylmethoxymethyl)-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione    (tefuryltrione),-   2-[2-chloro-3-[2-(2-methoxyethoxy)ethoxymethyl]-4-(ethylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   2-[2-chloro-3-[2-(2-methoxyethoxy)ethoxymethyl]-4-(methylsulfonyl)benzoyl]-1,3-cyclohexanedione,-   3-({2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)pyridin-3-yl}carbonyl)-bicyclo[3.2.1]octane-2,4-dione    (WO 2001094339);-   I) benzoylisoxazoles, for example-   5-cyclopropyl-[2-(methylsulfonyl)-4-(trifluoromethyl)benzoyl]isoxazole    (isoxaflutole);    (4-chloro-2-mesylphenyl)(5-cyclopropyl-1,2-oxazol-4-yl)methanone    (isoxachlortole);-   J) benzoylpyrazoles, for example-   2-[4-(2,4-dichloro-m-toluoyl)-1,3-dimethylpyrazol-5-yloxy]-4′-methylacetophenone    (benzofenap),-   4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl toluene-4-sulfonate    (pyrazolynate),-   2-[4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yloxy]acetophenone    (pyrazoxyfen);-   5-hydroxy-1-methyl-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole    (WO 01/74785 (U.S. Pat. No. 6,420,317)),-   1-ethyl-5-hydroxy-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole    (WO 01/74785),-   1,3-dimethyl-5-hydroxy-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole    (WO 01/74785),-   1-ethyl-5-hydroxy-3-methyl-4-[2-(methylsulfonyl)-4-trifluoromethylbenzoyl]pyrazole    (pyrasulfotole, WO 01/74785),-   5-hydroxy-1-methyl-4-[2-chlor-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonyl-benzoyl]pyrazole    (WO 99/58509 (U.S. Pat. No. 6,525,204)),-   5-hydroxy-1-methyl-4-[3-(4,5-dihydroisoxazol-3-yl)-2-methyl-4-methylsulfonyl-benzoyl]pyrazole    (topramezone, WO 99/58509),-   1-ethyl-5-hydroxy-3-methyl-4-[2-methyl-4-methylsulfonyl-3-(2-methoxyethylamino)-benzoyl]pyrazole    (WO 96/26206 (U.S. Pat. No. 5,846,907)),-   3-cyclopropyl-5-hydroxy-1-methyl-4-[2-methyl-4-methylsulfonyl-3-(2-methoxy-ethylamino)benzoyl]pyrazole    (WO 96/26206),-   5-benzoxy-1-ethyl-4-[2-methyl-4-methylsulfonyl-3-(2-methoxyethylamino)benzoyl]-pyrazole    (WO 96/26206),-   1-ethyl-5-hydroxy-4-(3-dimethylamino-2-methyl-4-methylsulfonylbenzoyl)pyrazole    (WO 96/26206),-   5-hydroxy-1-methyl-4-(2-chloro-3-dimethylamino-4-methylsulfonylbenzoyl)pyrazole    (WO 96/26206),-   1-ethyl-5-hydroxy-4-(3-allylamino-2-chloro-4-methylsulfonylbenzoyl)pyrazole    (WO 96/26206),-   1-ethyl-5-hydroxy-4-(2-methyl-4-methylsulfonyl-3-morpholinobenzoyl)pyrazole    (WO 96/26206),-   5-hydroxy-1-isopropyl-4-(2-chloro-4-methylsulfonyl-3-morpholinobenzoyl)pyrazole    (WO 96/26206),-   3-cyclopropyl-5-hydroxy-1-methyl-4-(2-chloro-4-methylsulfonyl-3-morpholino-benzoyl)pyrazole    (WO 96/26206),-   1,3-dimethyl-5-hydroxy-4-(2-chloro-4-methylsulfonyl-3-pyrazol-1-ylbenzoyl)pyrazole    (WO 96/26206),-   1-ethyl-5-hydroxy-3-methyl-4-(2-chloro-4-methylsulfonyl-3-pyrazol-1-ylbenzoyl)-pyrazole    (WO 96/26206),-   1-ethyl-5-hydroxy-4-(2-chloro-4-methylsulfonyl-3-pyrazol-1-ylbenzoyl)pyrazole    (WO 96/26206),-   (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-5-yl)methanone    (US2002/0016262),-   1-methyl-4-[(3,3,4-trimethyl-1,1-dioxido-2,3-dihydro-1-benzothien-5-yl)carbonyl]-1H-pyrazol-5-ylpropane-1-sulfonate    (US2002/0016262, WO 2002/015695 (US 2002052296));-   3-(2-chloro-4-mesylbenzoyl)-2-phenylthiobicyclo[3.2.1]oct-2-en-4-one    (benzobicyclon);-   K) sulfonylaminocarbonyltriazolinones, for example-   4,5-dihydro-3-methoxy-4-methyl-5-oxo-N-(2-trifluoromethoxyphenylsulfonyl)-1H-1,2,4-triazole-1-carboxamide    sodium salt (flucarbazone-sodium),-   methyl    2-(4,5-dihydro-4-methyl-5-oxo-3-propoxy-1H-1,2,4-triazol-1-yl)carboxamido-sulfonylbenzoate    sodium salt (propoxycarbazone-Na);-   methyl    4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo-1H-1,2,4-triazol-1-yl)carbonyl-sulfamoyl]-5-methylthiophene-3-carboxylate    (thiencarbazone-methyl);-   L) triazolinones, for example-   4-amino-N-tert-butyl-4,5-dihydro-3-isopropyl-5-oxo-1,2,4-1H-triazole-1-carboxamide    (amicarbazone),-   2-(2,4-dichloro-5-prop-2-ynyloxyphenyl)-5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]-pyridin-3(2H)-one    (azafenidin),-   ethyl    (RS)-2-chloro-3-[2-chloro-5-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-4-fluorophenyl]propionate    (carfentrazone-ethyl),-   2′,4′-dichloro-5′-(4-difluoromethyl-4,5-dihydro-3-methyl-5-oxo-1H-1,2,4-triazol-1-yl)-methanesulfonanilide    (sulfentrazone);-   4-[4,5-dihydro-4-methyl-5-oxo-3-(trifluoromethyl)-1H-1,2,4-triazol-1-yl]-2-[(ethylsulfonyl)amino]-5-fluorobenzenecarbothioamide    (bencarbazone);-   M) phosphinic acids and derivatives, for example-   4-[hydroxy(methyl)phosphinoyl]-L-homoalanyl-L-alanyl-L-alanine    (bilanafos), DL-homoalanin-4-yl(methyl)phosphinic acid ammonium salt    (glufosinate-ammonium);-   N) glycine derivatives, for example-   N-(phosphonomethyl)glycine and its salts (glyphosate and salts, for    example the sodium salt or the isopropylammonium salt),-   N-(phosphonomethyl)glycine trimesium salt (sulfosate);-   O) pyrimidinyloxypyridinecarboxylic acid derivatives;    pyrimidinyloxybenzoic acid derivatives and pyrimidinylthiobenzoic    acid derivatives, for example-   benzyl 3-(4,6-dimethoxypyrimidin-2-yl)oxypyridine-2-carboxylate    (EP-A 0 249 707 (U.S. Pat. No. 4,832,729)),-   methyl 3-(4,6-dimethoxypyrimidin-2-yl)oxypyridine-2-carboxylate    (EP-A 0 249 707),-   1-(ethoxycarbonyloxyethyl)    2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoate (EP-A 0 472 113    (U.S. Pat. No. 5,154,750)),-   2,6-bis[(4,6-dimethoxypyrimidin-2-yl)oxy]benzoic acid    (bispyribac-sodium),-   isopropyl    4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate    (pyribambenz-isopropyl, WO 2002034724 (U.S. Pat. No. 6,800,590)),-   propyl    4-[[[2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]phenyl]methyl]amino]benzoate    (pyribambenz-propyl, WO 2002034724),-   pyribenzoxim, pyriftalid, pyriminobac-methyl, pyrithiobac-sodium,    pyrimisulfan;-   P) S-(N-aryl-N-alkylcarbamoylmethyl)dithiophosphonic acid esters,    such as S-[N-(4-chlorophenyl)-N-isopropylcarbamoylmethyl]    O,O-dimethyl dithiophosphate (anilophos);-   Q) triazinones, for example-   3-cyclohexyl-6-dimethylamino-1-methyl-1,3,5-triazine-2,4-(1H,3H)-dione    (hexazinone),-   4-amino-4,5-dihydro-3-methyl-6-phenyl-1,2,4-triazin-5-one    (metamitron),-   4-amino-6-tert-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one    (metribuzin);-   R) pyridinecarboxylic acids, for example-   aminopyralid, clopyralid, fluoroxypyr, picloram and triclopyr;-   S) pyridines, for example-   dithiopyr and thiazopyr;-   T) pyridinecarboxamides, for example-   diflufenican and picolinafen;-   U) 1,3,5-triazines, for example-   ametryn, atrazine, cyanazine, dimethametrin, prometon, prometryn,    propazine, simazine, symetryn, terbumeton, terbuthylazine, terbutryn    and trietazine;-   V) plant growth regulators, for example-   forchlorfenuron and thidiazuron;-   W) ketoenoles, for example-   8-(2,6-diethyl-p-tolyl)-1,2,4,5-tetrahydro-7-oxo-7H-pyrazolo[1,2-d][1,4,5]oxadiazepin-9-yl    2,2-dimethylpropionate (pinoxaden);-   X) pyrazoles, for example-   3-[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-ylmethylsulfonyl]-4,5-dihydro-5,5-dimethyl-1,2-oxazole    (pyroxasulfone).

The herbicides of groups A to W are known, for example, from therespective abovementioned publications and from “The Pesticide Manual”,The British Crop Protection Council, 14th Edition, 2006, or thee-Pesticide Manual, Version 4.0, British Crop Protection Council 2006 orelse from the “Compendium of Pesticide Common Names”.

When used as active compound formulations or coformulations, theygenerally comprise, if appropriate, the respective customary tackifiers,wetting agents, dispersing agents, emulsifiers, penetrants,preservatives, antifreeze agents and solvents, fillers, carriers andcolorants, antifoams, evaporation inhibitors and pH- andviscosity-modifying agents.

The compounds of the formula I and their combinations with one or moreof the abovementioned pesticides can be formulated in various ways,depending on the prevailing physicochemical and biological parameters.Examples of suitable formulation types are:

-   -   emulsifiable concentrates which are prepared by dissolving the        active compounds in an organic solvent, for example butanol,        cyclohexanone, dimethylformamide, xylene or else relatively        high-boiling hydrocarbons or mixtures of the organic solvents        with addition of one or more ionic and/or nonionic surfactants        (emulsifiers). Suitable emulsifiers are, for example, calcium        alkylarylsulfonates, fatty acid polyglycol esters, alkylaryl        polyglycol ethers, fatty alcohol polyglycol ethers, propylene        oxide/ethylene oxide condensates, alkyl polyethers, sorbitan        esters and polyoxyethylenesorbitan fatty acid esters;    -   dusts, which are obtained by grinding the active compounds with        finely dispersed solid inorganic or organic substances, for        example talc, natural clays, such as kaolin, bentonite and        pyrophyllite, diatomaceous earth or meals;    -   water- or oil-based suspension concentrates, which can be        prepared, for example, by wet grinding using bead mills;    -   water-soluble powders;    -   water-soluble concentrates;    -   granules, such as water-soluble granules, water-dispersible        granules and granules for application by broadcasting and soil        application;    -   wettable powders which, in addition to active compound, also        contain diluents or inert substances and surfactants;    -   capsule suspensions and microcapsules;    -   ultra-low-volume formulations.

The abovementioned formulation types are known to the person skilled inthe art and described, for example, in: K. Martens, “Spray DryingHandbook”, 3rd Ed., G. Goodwin Ltd., London, 1979; W. van Valkenburg,“Pesticide Formulations”, Marcel Dekker, N.Y. 1973; Winnaker-Küchler,“Chemische Technologie” [Chemical Technology], volume 7, C. HanserVerlag Munich, 4th edition 1986; “Perry's Chemical Engineer's Handbook”,5th Ed., McGraw-Hill, N.Y. 1973, pages 8-57.

The formulation auxiliaries required, such as inert materials,surfactants, solvents and other additives are also known and aredescribed, for example, in: McCutcheon's “Detergents and EmulsifiersAnnual”, MC Publ. Corp., Ridgewood N.J.; C. Marsden, “Solvents Guide”,2nd Ed., Interscience, N.Y. 1963; H. von Olphen, “Introduction to ClayColloid Chemistry”, 2nd Ed., J. Wiley & Sons, N.Y.; Schönfeldt,“Grenzflächenaktive Äthylenoxidaddukte” [Surface-active ethylene oxideadducts], Wiss. Verlagsgesellschaft, Stuttgart 1976; Sisley and Wood,“Encyclopedia of Surface Active Agents”, Chem. Publ. Co. Inc., N.Y.1964; Watkins, “Handbook of Insecticide Dust Diluents and Carriers”, 2ndEd., Darland Books, Caldwell N.J.; Winnacker-Küchler, “ChemischeTechnologie” [Chemical Technology], volume 7, C. Hanser Verlag Munich,4th edition 1986.

In addition to the abovementioned formulation auxiliaries, theuseful-plant-protecting compositions may comprise, if appropriate,customary tackifiers, wetting agents, dispersants, penetrants,emulsifiers, preservatives, antifreeze agents, fillers, carriers,colorants, anti-foams, evaporation inhibitors and pH or viscosityregulators.

Depending on the formulation type, the useful-plant-protectingcompositions generally comprise 0.1 to 99% by weight, in particular 0.2to 95% by weight, of one or more safeners of the formula I or acombination of safener and pesticide. Furthermore, they comprise 1 to99.9, in particular 4 to 99.5,% by weight of one or more solid or liquidadditives and 0 to 25, in particular 0.1 to 25,% by weight of asurfactant. In emulsifiable concentrates, the concentration of activecompound, i.e. the concentration of safener and/or pesticide, isgenerally 1 to 90, in particular 5 to 80,% by weight. Dusts usuallycomprise 1 to 30, preferably 5 to 20,% by weight of active compound. Inwettable powders, the concentration of active compound is generally 10to 90% by weight. In water-dispersible granules, the content of activecompound is, for example, between 1 and 95% by weight, preferablybetween 10 and 80% by weight.

For use, the formulations, which are present in commercially availableform, are, if appropriate, diluted in a customary manner, for example inthe case of wettable powders, emulsifiable concentrates, dispersions andwater-dispersible granules, with water. Preparations in the form ofdusts, granules and sprayable solutions are usually not diluted with anyfurther inert substances prior to use. The required application rate ofthe safeners varies with the external conditions such as, inter alia,temperature, humidity and the type of herbicide used.

In the examples below, which illustrate the invention but do not limitit, the amounts are based on weight, unless defined otherwise.

EXAMPLES 1 Formulation Examples 1.1 DUSTING AGENT

A dusting agent is obtained by mixing 10 parts by weight of a compoundof the formula (I) or of an active compound mixture of a pesticide (eg.herbicide) and a safener of the formula (I) and 90 parts by weight oftalc as inert material and comminuting in a hammer mill.

1.2 Water-Dispersible Powder

A wettable powder which is readily dispersible in water is obtained bymixing 25 parts by weight of a compound of the formula (I) or of anactive compound mixture of a pesticide (eg. herbicide) and a safener ofthe formula (I), 64 parts by weight of kaolin-containing quartz as inertmaterial, 10 parts by weight of potassium ligninsulfonate and 1 part byweight of sodium oleoylmethyltaurinate as wetting and dispersing agent,and grinding in a pin mill.

1.3 Water-Dispersible Concentrate

A dispersion concentrate which is readily dispersible in water isobtained by mixing 20 parts by weight of a compound of the formula (I)or of an active compound mixture of a pesticide (eg. herbicide) and asafener of the formula (I) with 6 parts by weight of alkylphenolpolyglycol ether (®Triton X 207), 3 parts by weight of isotridecanolpolyglycol ether and 71 parts by weight of paraffinic mineral oil andgrinding in a ball mill to a fineness of below 5 microns.

1.4 Emulsifiable Concentrate

An emulsifiable concentrate is obtained from 15 parts by weight of acompound of the formula (I) or of an active compound mixture of apesticide (eg. herbicide) and a safener of the formula (I), 75 parts byweight of cyclohexanone as solvent and 10 parts by weight of ethoxylatednonylphenol as emulsifier.

1.5 Water-Dispersible Granules

Water-dispersible granules are obtained by mixing

75 parts by weight  of a safener of the formula (I) or of a mixture of apesticide and a safener of the formula (I), 10 parts by weight  ofcalcium ligninsulfonate, 5 parts by weight of sodium lauryl sulfate, 3parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin,grinding in a pin mill and granulating the powder in a fluidized bed byspraying on water as granulation liquid.

Water-dispersible granules are also obtained by homogenizing

25 parts by weight of a safener of the formula (I) or of a mixture of apesticide and a safener of the formula (I),  5 parts by weight of sodium2,2′-dinaphthylmethane-6,6′-disulfonate,  2 parts by weight of sodiumoleoylmethyltaurinate, 17 parts by weight of calcium carbonate, 50 partsby weight of water and 1 part by weight of polyvinyl alcoholin a colloid mill, comminuting, then grinding in a bead mill andatomizing and drying the resulting suspension in a spray tower using asingle-fluid nozzle.

2. Preparation Examples Example A1

N-Cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamideA1.1) 4-Butoxy-1,1,1-trifluorobut-3-en-2-one

At 5° C., 79.9 g (0.38 mol) of trifluoroacetic anhydride—dissolved in100 ml of trichloromethane—were added with stirring to a mixture of 29.9g (0.38 mol) of pyridine and 50.0 g (0.38 mol) of butyl vinyl ether in200 ml of trichloromethane. After the addition, stirring was continuedat room temperature for another 15 h. 300 ml of water were then added tothe mixture, and the organic phase was separated off, dried andconcentrated. This gave 59 g (79% of theory) of a yellowish oil. ¹H-NMR:[CDCl₃] 0.96 (t, 3H); 1.41 (m, 2H); 1.73 (m, 2H); 4.04 (t, 2H); 5.85 (d,1H); 7.90 (d, 1H).

A1.2) Methyl 2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate

2.15 g (94 mmol) of sodium were dissolved in 300 ml of methanol, 15.3 g(78 mmol) of 4-butoxy-1,1,1-trifluorobut-3-en-2-one and 9.13 g (78 mmol)of methyl malonate-monoamide were added and the mixture was heated underreflux for 18 h. The mixture was concentrated, and the residue was takenup in water and washed with dichloromethane. The aqueous phase was thenadjusted to pH 2 by addition of 2N hydrochloric acid and extracted withdichloromethane. Drying and concentration of the extract gave 12 g (69%of theory) of a colorless powder.

¹H-NMR: [CDCl₃] 4.03 (s, 3H); 7.31 (d, 1H); 8.39 (d, 1H).

A1.3) 2-Oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid

At room temperature, 4.73 g (21.4 mmol) of methyl2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate weredissolved in 45 ml of methanol and 15 ml of water, 1.80 g (42.8 mmol) oflithium hydroxide monohydrate were added and the mixture was then heatedunder reflux for 2 h. The mixture was concentrated to about 15 ml andthen washed with dichloromethane and the aqueous phase was adjusted topH 2 by addition of 2N hydrochloric acid. The mixture was againextracted with dichloromethane, and the organic phase was dried andconcentrated. This gave 4.2 g (94% of theory) of a colorless powder.

¹H-NMR: [DMSO] 7.41 (d, 1H); 8.35 (d, 1H).

A1.4)N-Cyclobutyl-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

600 mg (2.9 mmol) of2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylic acid weredissolved in 5 ml of tetrahydrofuran, 658 mg (4.1 mmol) ofN,N-carbonyldiimidazole were added and the mixture was heated initiallyat room temperature for 30 min and then under reflux for 30 min. Asolution of 247 mg (3.5 mmol) of cyclobutylamine in 5 ml tetrahydrofuranwas then added dropwise, and the mixture was heated under reflux for afurther 2 h. The solution was evaporated to dryness and then taken up inethyl acetate, washed with 1 N hydrochloric acid and water, dried andconcentrated. Purification by column chromatography gave 160 mg (19% oftheory) of a light-brown powder.

¹H-NMR: [CDCl₃] 1.80 (m, 2H); 2.00 (m, 2H); 2.42 (m, 2H); 4.55 (m, 1H);6.88 (d, 1H); 8.65 (d, 1H); 9.50 (br, 1H).

Example A2

6-[Chloro(difluoro)methyl]-N-(2-methoxyethyl)-2-oxo-1,2-dihydropyridine-3-carboxamideA2.1) 4-Butoxy-1-chloro-1,1-difluorobut-3-en-2-one

Under stirring at 5° C., 5.0 g (20.2 mmol) of chlorodifluoroaceticanhydride—dissolved in 10 ml of trichloromethane—were added to a mixtureof 1.60 g (20.2 mmol) of pyridine and 2.1 g (20.2 mmol) of butyl vinylether in 30 ml of trichloromethane. After the addition, stirring wascontinued at room temperature for another 15 h. 100 ml of water werethen added to the mixture, and the organic phase was separated off,dried and concentrated. This gave 3.4 g (80% of theory) of a yellowishoil.

¹H-NMR: [DMSO] 0.90 (t, 3H); 1.35 (m, 2H); 1.65 (m, 2H); 4.20 (t, 2H);6.04 (d, 1H); 8.10 (d, 1H).

A2.2) Methyl6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylate

1.47 g (61 mmol) of sodium were dissolved in 220 ml of methanol, 10 g(47 mmol) of 4-butoxy-1-chloro-1,1-difluorobut-3-en-2-one and 5.51 g (47mmol) of methyl malonatemonoamide were added and the mixture was heatedunder reflux for 21 h. The pH was adjusted to 4-5 by addition of 2Nhydrochloric acid, and about 200 ml were then distilled off. Thesolution that remained was extracted with ethyl acetate, and the extractwas dried and concentrated. The residue was triturated with diisopropylether, filtered off with suction and dried. This gave 7.4 g (66% oftheory) of a colorless powder.

¹H-NMR: [CDCl₃] 4.01 (s, 3H); 7.30 (d, 1H); 8.38 (d, 1H); 11.5 (br, 1H).

A2.3a) 6-[Chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylicacid

1.70 g (74 mmol) of sodium were dissolved in 250 ml of methanol, 13.1 g(61.7 mmol) of 4-butoxy-1-chloro-1,1-difluorobut-3-en-2-one and 7.22 g(61.7 mmol) of methyl malonatemonoamide were added and the mixture washeated under reflux for 21 h. 250 ml of water and 2.9 g (67.9 mmol) oflithium hydroxide monohydrate were then added, and heating under refluxwas continued for a further 2 h. The mixture was concentrated to about200 ml and washed with dichloromethane, and the aqueous phase wasacidified with 2N hydrochloric acid to pH 2. The precipitated solid wasfiltered off with suction and dried under reduced pressure. 9.3 g (68%of theory).

A2.3b) 6-[Chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylicacid

11.0 g (49.4 mmol) of6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxamide wereheated in 77 ml of 50% strength sulfuric acid. The mixture was thenadded to ice water, and the precipitate was filtered off with suctionand dried. This gave 7.2 g (65% of theory) of a yellowish powder.

m.p.: 145-147° C.

¹H-NMR: [DMSO] 7.36 (d, 1H); 8.34 (d, 1H).

A2.4)6-[Chloro(difluoro)methyl]-N-(2-methoxyethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

500 mg (2.2 mmol) of6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acidwere dissolved in 10 ml of tetrahydrofuran, 508 mg (3.1 mmol) ofN,N-carbonyldiimidazole were added and the mixture was then stirredinitially at room temperature for 30 min and then under reflux for 30min. A solution of 202 mg (2.7 mmol) of 2-methoxyethylamine in 2 ml oftetrahydrofuran was then added dropwise, and the mixture was heatedunder reflux for a further 2 h. The solution was evaporated to dryness,the residue was taken up in ethyl acetate and the solution was washedwith 1 N hydrochloric acid and water, dried and concentrated. This gave360 mg (54% of theory) of a light-brown powder.

¹H-NMR: [CDCl₃] 3.40 (s, 3H); 3.58 (m, 2H); 3.67 (m, 2H); 6.84 (d, 1H),8.62 (d, 1H); 9.40 (br, 1H).

Example A3

MethylN-({6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridin-3-yl}carbonyl)glycinate

300 mg (1.34 mmol) of6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylic acidwere dissolved in 5 ml of tetrahydrofuran, 435 mg (2.68 mmol) ofN,N-carbonyldiimidazole were added and the mixture was stirred initiallyat room temperature for 30 min and then under reflux for 30 min. Amixture of 168 mg (1.34 mmol) of glycine methyl ester hydrochloride in 3ml of tetrahydrofuran was then added, and the mixture was heated underreflux for a further 2 h. The solution was evaporated to dryness, theresidue was taken up in ethyl acetate and the solution was washed with 1N hydrochloric acid and water, dried and concentrated. This gave 92 mg(23% of theory) of a light-brown powder.

¹H-NMR: [DMSO] 3.65 (s, 3H); 4.12 (d, 2H); 7.28 (d, br, 1H); 8.42 (d,1H); 9.25 (t, br, 1H), 13.6 (br, 1H)

Example A4

N-(1-Methylpropyl)-2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamideA4.1) 1-Butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one

With stirring at −10° C., 17.0 g (93.2 mmol) of pentafluoropropionylchloride -dissolved in 20 ml of dichloromethane—were added to a mixtureof 8.11 g (102 mmol) pyridine and 9.33 g (93.2 mmol) of butyl vinylether in 200 ml of dichloromethane. After the addition, stirring wascontinued at room temperature for a further 15 h. 200 ml of water werethen added to the mixture, and the organic phase was separated off,dried and concentrated. This gave 18.9 g (82% of theory) of a yellowishoil.

¹H-NMR: [DMSO] 0.85 (t, 3H); 1.32 (m, 2H); 1.63 (m, 2H); 4.20 (t, 2H);6.06 (d, 1H); 8.11 (d, 1H).

A4.2) Ethyl 2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxylate

0.56 g (24.4 mmol) of sodium was dissolved in 150 ml of ethanol, 5 g(20.3 mmol) of 1-butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one and 2.66 g(20.3 mmol) of methyl malonatemonoamide were added and the mixture washeated under reflux for 6 h. The mixture was concentrated to about 50ml, 500 ml of 1 N hydrochloric acid were added and the mixture was thenextracted with ethyl acetate. Drying and concentration gave 2.3 g (40%of theory) of a yellowish resin.

¹H-NMR: [CDCl₃] 1.45 (t, 3H); 4.50 (q, 2H); 7.35 (d, 1H); 8.40 (d, 1H);11.4 (br, 1H).

A4.3)N-(1-Methylpropyl)-2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide

At room temperature, 160 mg (0.56 mmol) of ethyl2-oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxylate werestirred in 5 ml of 2-butylamine for 14 h. The pH was then adjusted to 2by addition of 1 N hydrochloric acid, which resulted in theprecipitation of a colorless solid. Filtration with suction and dryinggave 160 mg (91% of theory) of the product.

¹H-NMR: [CDCl₃] 0.97 (t, 3H); 1.22 (d, 3H); 1.59 (m, 2H); 4.10 (m, 1H);6.88 (d, 1H); 8.72 (d, 1H); 9.24 (d, br, 1H); 13.6 (br).

Example A5

2-Oxo-6-(pentafluoroethyl)-1,2-dihydropyridine-3-carboxamide

0.22 g (9.7 mmol) of sodium was dissolved in 50 ml of ethanol, 2 g (8.1mmol) of 1-butoxy-4,4,5,5,5-pentafluoropent-1-en-3-one and 0.86 g (8.1mmol) malonamide were added and the mixture was heated under reflux for7 h. The mixture was concentrated, and 1 N hydrochloric acid was added.The resulting precipitate was filtered off with suction and dried. Thisgave 1.9 g (94% of theory) of a yellow powder.

¹H-NMR: [DMSO] 7.45 (d, 1H); 8.15 (br, 1H); 8.45 (br, 1H); 8.50 (d, 1H);13.7 (br, 1H).

Example A6

N-[(Dimethylamino)methylene]-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

0.87 g (7.28 mmol) of N,N-dimethylformamide dimethyl acetal was added to1.00 g (4.85 mmol) of2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide in 5 ml oftoluene, and the mixture was heated under reflux for 4 h. After cooling,the resulting precipitate was filtered off with suction and dried: 0.5 g(39% of theory).

¹H-NMR: [CDCl₃] 3.25 (s, 3H); 3.35 (3, 3H); 7.25 (d, 1H); 8.58 (d, 1H);8.76 (s, 1H) ¹³C-NMR. [CDCl₃] 35 (NMe₂); 106 (C-5); 115 (C-3); 122 (q,CF₃); 143 (C-4); 151 (C-6); 164 (N═CN); 167 (C-2); 171 (CON).

Example A7

5-Chloro-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

At room temperature, 0.39 g (2.9 mmol) of sulfuryl chloride was added to300 mg (1.46 mmol) of2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide in 5 ml of1,2-dichloroethane and 2.3 g (0.25 ml) of pyridine, and the mixture wasthen heated under reflux for 2 h. The mixture was then added to 0.5Nhydrochloric acid. The organic phase was removed and then dried andconcentrated, which gave 144 mg (41% of theory) of a brownish powder.

¹H-NMR: [DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.50 (s, 1H); 13.8 (br, 1H)

¹³C-NMR. [DMSO] 118 (C-5); 120 (C-6),: 120.5 (q, CF₃); 144 (C-4), 161(C-2); 166 (COONH₂).

Example A8

N-Allyl-5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamideA8.1) Methyl5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate

At room temperature, 0.36 g (2.04 mmol) of N-bromosuccinimide was addedto a suspension of 0.3 g (1.36 mmol) of methyl2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate in 10 ml ofglacial acetic acid, and the mixture was then heated under reflux for 2days. The reaction mixture was then added to water and extracted withdichloromethane. The extract was concentrated, and the residue waspurified further by preparative HPLC. This gave 227 mg (56% of theory)of a colorless powder.

¹H-NMR: [DMSO] 3.85 (s, 3H); 8.45 (s, 1H); 12.80 (br, 1H);

¹³C-NMR. [DMSO] 53 (OCH₃); 105 (C-3); 148 (C-4),161 (C-2); 164 (COOMe).

A8.2)N-Allyl-5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxamide

At room temperature, 250 mg (0.83 mmol) of methyl5-bromo-2-oxo-6-(trifluoromethyl)-1,2-dihydropyridine-3-carboxylate werestirred in 5 ml of allylamine for 18 h. By addition of 2N hydrochloricacid, the pH was then adjusted to 2, resulting in the precipitation of acolorless solid. Filtration with suction and drying gave 134 mg (50% oftheory) of the product.

¹H-NMR: [DMSO] 3.94 (t, 2H); 5.18 (dd, 2H); 5.89 (m, 1H); 8.52 (s, 1H);8.85 (t, br, 1H).

Example A9

6-Difluoromethyl-N-isopropyl-2-oxo-1,2-dihydropyridine-3-carboxamideA9.1) 4-Butoxy-1,1-difluorobut-3-en-2-one

With stirring at 5° C., 10.0 g (55.7 mmol) of difluoroacetic anhydridewere added to a mixture of 4.41 g (4.5 ml, 55.7 mmol) of pyridine and5.7 g (55.7 mmol) butyl vinyl ether in 330 ml of trichloromethane. Afterthe addition, stirring was continued at room temperature for a further15 h. 300 ml of water were then added to the mixture, and the organicphase was separated off, dried and concentrated. This gave 5.7 g (57% oftheory) of a yellowish oil.

¹H-NMR: [CDCl₃] 0.95 (t, 3H); 1.42 (m, 2H); 1.72 (m, 2H); 4.00 (t, 2H);5.78 (t, 1H); 5.90 (d, 1H); 7.85 (d, 1H).

A9.2) Methyl 6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

1.21 g (52.9 mmol) of sodium were dissolved in 200 ml of methanol, 7.9 g(44 mmol) of 4-butoxy-1,1-difluorobut-3-en-2-one and 5.3 g (44 mmol) ofmethyl malonatemonoamide were then added and the mixture was heatedunder reflux for 15h. The mixture was concentrated and the residue wasthen triturated with 100 ml of 1 N hydrochloric acid. The solid obtainedwas filtered off with suction and dried: 7.4 g (82% of theory).

¹H-NMR: [DMSO] 3.82 (s, 3H); 6.85 (t, 1H); 7.02 (d, br, 1H); 8.20 (d,1H); 12.4 (br, 1H).

A9.3) 6-(Difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

7.4 g (36.4 mmol) of methyl6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate weredissolved in 100 ml of methanol, and a solution of 1.3 g (54.6 mmol) oflithium hydroxide in 50 ml of water was added. After two hours ofheating under reflux, the mixture was concentrated to a volume of about50 ml and the solution was washed with dichloromethane. The aqueousphase was then acidified with 2N hydrochloric acid and extracted withethyl acetate. Drying and concentration of the extract gave 5.6 g (82%of theory) of a brownish powder.

A9.4)6-(Difluoromethyl)-N-isopropyl-2-oxo-1,2-dihydropyridine-3-carboxamide

After dissolution of 200 mg (1.1 mmol) of6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid in 25 mlof tetrahydrofuran and addition of 206 mg (1.3 mmol) ofN,N-carbonyldiimidazole, the mixture was stirred initially at roomtemperature for 30 min and then under reflux for 30 min. A solution of66 mg (1.1 mmol) of isopropylamine in 5 ml of tetrahydrofuran was thenadded dropwise, and the mixture was heated under reflux for a further 2h. The solution was evaporated to dryness, the residue was then taken upin ethyl acetate and the mixture was washed with 2N hydrochloric acidand water, dried and concentrated. Purification by column chromatographygave 150 mg (61% of theory) of a colorless powder.

¹H-NMR: [CDCl₃] 1.25 (d, 6H); 4.22 (m, 1H); 6.55 (t, 1H); 6.69 (d, 1H);8.64 (d, 1H); 9.42 (d, br, 1H); 13.0 (br, 1H).

Example A10

6-(Heptafluoropropyl)-2-oxo-N-propyl-1,2-dihydropyridine-3-carboxamideA10.1) 1-Butoxy-4,4,5,5,6,6,6-heptafluorohex-1-en-3-one

With stirring and at −10° C., 21.7 g (93.2 mmol) of heptafluorobutyrylchloride—dissolved in 50 ml of dichloromethane—were added to a mixtureof 8.11 g (102 mmol) of pyridine and 9.33 g (93.2 mmol) of butyl vinylether in 200 ml of dichloromethane. After the addition, stirring wascontinued at room temperatur for another 15 h. 300 ml of water were thenadded to the mixture, and the organic phase was separated off, dried andconcentrated.

This gave 28.2 g (82% of theory) of a yellowish oil which was reactedfurther without further purification.

¹H-NMR: [CDCl₃] 0.96 (t, 3H); 1.40 (m, 2H); 1.75 (m, 2H); 4.04 (t, 2H);5.95 (d, 1H); 7.93 (d, 1H).

A10.2) Methyl6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

After dissolution of 2.63 g (114 mmol) of sodium in 250 ml of methanol,28.2 g (95.5 mmol) of 1-butoxy-4,4,5,5,6,6,6-heptafluorohex-1-en-3-oneand 11.18 g (95.5 mmol) of methyl malonatemonoamide were added, and themixture was heated under reflux for 18 h. The mixture was concentratedand the residue was then taken up in water and washed withdichloromethane. The aqueous phase was then adjusted to pH 2 by additionof 2N hydrochloric acid and extracted with dichloromethane. Drying,concentration and purification of the extract by column chromatographygave 15.2 g (49% of theory) of a yellow powder.

¹H-NMR: [CDCl₃] 4.06 (s, 3H); 7.35 (d, 1H); 8.40 (d, 1H); 11.4 (br, 1H).

A10.3)6-(Heptafluoropropyl)-2-oxo-N-propyl-1,2-dihydropyridine-3-carboxamide

250 mg (0.78 mmol) of methyl6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate in 5 ml ofpropylamine were heated under reflux for 5 h. The mixture was thenadjusted to pH 2 by addition of 1 N hydrochloric acid and extracted withdichloromethane. Drying and concentration gave 240 mg (88% of theory) ofa beige powder.

¹H-NMR: [DMSO] 0.90 (t, 3H); 1.54 (m, 2H); 3.25 (q, 2H); 7.41 (d, 1H);8.40 (d, 1H); 8.85 (br, 1H); 13.45 (br, 1H).

Example A11

N-Methyl-2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxamideA11.1) 1-Butoxy-4,4,5,5-tetrafluoropent-1-en-3-one

With stirring and at 0° C., 25.0 g (152 mmol) of 3H-tetrafluoropropionylchloride—dissolved in 20 ml dichloromethane—were added to a mixture of14.4 g (182 mmol) of pyridine and 15.2 g (152 mmol) of butyl vinyl etherin 250 ml of dichloromethane. After the addition, stirring was continuedat room temperature for another 15 h. 250 ml of water were then added tothe mixture, and the organic phase was separated off, dried andconcentrated. This gave 12.5 g (36% of theory) of a yellowish oil.

¹H-NMR: [CDCl₃] 0.96 (t, 3H); 1.46 (m, 2H); 1.75 (m, 2H); 4.03 (t, 2H);6.00 (d, 1H); 6.09 (tt, 1H); 7.90 (d, 1H).

A11.2) Methyl2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxylate

After dissolution of 1.39 g (60.3 mmol) of sodium in 500 ml of methanol,11.5 g (50.3 mmol) of 1-butoxy-4,4,5,5-tetrafluoropent-1-en-3-one and6.07 g (50.3 mmol) of methyl malonatemonoamide were added, and themixture was heated under reflux for 6 h. The mixture was concentrated toabout 100 ml, 500 ml of 1 N hydrochloric acid were then added and themixture was subsequently extracted with ethyl acetate. Drying andconcentration gave 10.3 g (67% of theory) of a yellowish resin.

¹H-NMR: [CDCl₃] 4.03 (s, 3H); 6.40 (tt, 1H); 7.38 (d, 1H); 8.39 (d, 1H).

A11.3)N-Methyl-2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxamide

At room temperature, 300 mg (1.19 mmol) of methyl2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxylatewere stirred in 3.3 ml of a 40% strength aqueous methylamine solutionfor 14 h. The pH was then adjusted to 2 by addition of 1 N hydrochloricacid, and the mixture was extracted with dichloromethane. Drying andconcentration of the extract gave 230 mg (77% of theory) of the product.

¹H-NMR: [DMSO] 2.83 (d, 3H); 6.81 (tt, 1H); 7.22 (br, 1H); 8.41 (d, 1H);9.00 (br, 1H); 13.4 (br, 1H).

Example A12

2-Oxo-N-(2-propynyl)-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxamide

At room temperature, 300 mg (1.19 mmol) of methyl2-oxo-6-(1,1,2,2-tetrafluoroethyl)-1,2-dihydropyridine-3-carboxylatewere stirred in 3.3 ml (41 mmol) of propargylamine for 14 h. The pH wasthen adjusted to 2 by addition of 1 N hydrochloric acid, and the mixturewas extracted with dichloromethane. Drying and concentration of theextract gave 280 mg (85% of theory) of the product.

¹H-NMR: [DMSO] 3.15 (t, 1H); 4.13 (m, 2H); 6.82 (tt, 1H); 7.18 (br, 1H);8.41 (d, 1H); 9.35 (br, 1H); 13.3 (br, 1H).

Example A13

5-Bromo-6-(difluoromethyl)-N-(2-methoxy-1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamideA13.1) Methyl5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

4.1 g (20 mmol) of methyl6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate weredissolved in 20 ml of N,N-dimethylformamide, and 5.35 g (30 mmol) ofN-bromosuccinimide were added at room temperature. After 2 hours ofstirring, the reaction mixture was added to water and extracted withtert-butyl methyl ether. The extract was subsequently washed repeatedlywith water. Drying and concentration finally gave 3.7 g (65% of theory)of the product.

¹H-NMR: [DMSO] 3.83 (s, 3H); 7.07 (t, 1H); 8.34 (s, 1H); 12.5 (s, br,1H).

A13.2)5-Bromo-6-(difluoromethyl)-N-(2-methoxy-1-methylethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

At room temperature, 334 mg (1.19 mmol) of methyl5-bromo-6-(difluoromethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate in3.3 ml (41 mmol) of 2-amino-1-methoxy-propane were stirred for 14 h. ThepH was then adjusted to 2 by addition of 1 N hydrochloric acid, and themixture was extracted with dichloromethane. Drying and concentration ofthe extract gave 360 mg (89% of theory) of the product.

¹H-NMR: [CDCl₃] 1.27 (d, 3H); 3.40 (s, 3H); 3.43 (m, 2H); 4.37 (m, 1H);6.85 (t, 1H); 8.68 (s, 1H); 9.42 (d, br, 1H); 12.7 (br, 1H).

Example A14

5-Bromo-6-[chloro(difluoro)methyl]-N-(cyclopropylmethyl)-2-oxo-1,2-dihydropyridine-3-carboxamideA14.1) Methyl5-bromo-6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylate

1.30 g (5.47 mmol) of methyl6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridinecarboxylate weredissolved in 50 ml of N,N-dimethylformamide, and 1.46 g (8.21 mmol) ofN-bromosuccinimide were added at room temperature. After 3 hours ofstirring, the reaction mixture was added to water, resulting in theformation of a colorless precipitate. Drying and concentration gave 1.23g (71% of theory) of the product.

¹H-NMR: [DMSO] 3.85 (s, 3H); 8.45 (s, 1H); 12.7 (s, br, 1H).

A14.2)5-Bromo-6-[chloro(difluoro)methyl]-N-(cyclopropylmethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

At room temperature, 350 mg (1.11 mmol) of methyl5-bromo-6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-3-carboxylatewere dissolved in 5 ml of acetonitrile and stirred with 0.5 ml ofaminomethylcyclopropane for 12 h. The reaction mixture was then added to1 N hydrochloric acid, and the resulting precipitate was filtered offwith suction. The precipitate was dried, again triturated with 1 Nhydrochloric acid, filtered off with suction and washed with water.Drying gave 240 mg (62% of theory) of the product.

¹H-NMR: [DMSO] 0.25 (m, 2H); 0.46 (m, 2H); 1.04 (m, 1H); 3.20 (t, 2H);8.55 (s, 1H); 8.82 (t, br, 1H); 13.6 (br, 1H).

Example A15

6-[Chloro(difluoro)methyl]-N-(1-ethylpropyl)-5-iodo-2-oxo-1,2-dihydropyridine-3-carboxamideA15.1) Methyl6-[chloro(difluoro)methyl]-5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylate

10.0 g (42.1 mmol) of methyl6-[chloro(difluoro)methyl]-2-oxo-1,2-dihydropyridine-carboxylate weredissolved in 50 ml of N,N-dimethylformamide, and 6.32 g (63.1 mmol) ofcalcium carbonate and 20.5 g (126 mmol) of iodine chloride were added atroom temperature. After 6 hours of stirring at 50° C., the reactionmixture was added to water, resulting in the formation of a colorlessprecipitate, which was washed with dilute sodium bisulfite solution andwater. Filtration with suction and drying gave 13.6 g (89% of theory) ofthe product.

¹H-NMR: [DMSO] 3.84 (s, 3H); 8.61 (s, 1H); 12.6 (s, br, 1H).

A15.2)6-[Chloro(difluoro)methyl]-N-(1-ethylpropyl)-5-iodo-2-oxo-1,2-dihydro-pyridine-3-carboxamide

At room temperature, 400 mg (1.1 mmol) of methyl6-[chloro(difluoro)methyl]-5-iodo-2-oxo-1,2-dihydropyridine-3-carboxylatewere dissolved in 5 ml of acetonitrile and stirred with 0.5 ml of3-pentylamine for 12 h. The reaction mixture was then added to 1 N ofhydrochloric acid, and the resulting precipitate was filtered off withsuction and washed with water. Drying gave 370 mg (72% of theory) of theproduct.

¹H-NMR: [DMSO] 0.87 (t, 6H); 1.43 (m, 2H); 1.55 (m, 2H); 3.78 (m, 1H);8.55 (br, 1H); 8.67 (s, 1H); 13.5 (br, 1H).

Example A16

5-Chloro-N,N-diethyl-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxamideA16.1) Methyl5-chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

16.7 g (52 mmol) of methyl6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylate weredissolved in 160 ml of N,N-dimethylformamide, and 7.08 g (52 mmol) ofN-chlorosuccinimide were added at room temperature. After 3 hours ofstirring at 50° C., the reaction mixture was added to water andextracted repeatedly with ethyl acetate. The organic phase was thenseparated off, washed with water and dried. The resulting crude productwas then purified by preparative RP-HPLC. This gave 10.1 g (54% oftheory) of the product as a colorless powder.

¹H-NMR: [DMSO] 3.85 (s, 3H); 8.35 (s, 1H); 12.8 (s, br, 1H).

A16.2)5-Chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylicacid

1.54 g (4.33 mmol) of methyl5-chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylatewere dissolved in 23 ml of methanol, and a solution of 0.16 g (6.5 mmol)of lithium hydroxide in 13 ml of water was added. After two hours ofheating under reflux, the methanol was distilled off, and the aqueoussolution that remained was washed with dichloromethane. The aqueousphase was then acidfied with 2N hydrochloric acid and extracted withdichloromethane. Drying and concentration of the extract gave 1.45 g(98% of theory) of a brownish powder.

¹H-NMR: [DMSO] 8.30 (s, 1H).

A16.3)5-Chloro-N,N-diethyl-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

After dissolution of 355 mg (1.04 mmol) of5-chloro-6-(heptafluoropropyl)-2-oxo-1,2-dihydropyridine-3-carboxylicacid in 30 ml tetrahydrofuran and addition of 337 mg (2.08 mmol) ofN,N-carbonyldiimidazole, the mixture was stirred initially at roomtemperature for 30 min and then under reflux for 30 min. 152 mg (0.22ml, 2.08 mmol) of diethylamine were then added, and the mixture washeated under reflux for a further 2 h. The solution was evaporated todryness and then taken up in dichloromethane, washed with 1 Nhydrochloric acid and water, dried and concentrated. This gave 300 mg(72% of theory) of the product.

¹H-NMR: [DMSO] 1.03 (t, 3H); 1.15 (t, 3H); 3.12 (q, 2H); 3.45 (q, 2H);8.05 (s, 1H); 12.5 (br, 1H).

Example A17

6-(2-Chloro-1,1,2,2-tetrafluoroethyl)-N-ethyl-2-oxo-1,2-dihydropyridine-3-carboxamideA17.1) 1-Butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one

With stirring and at 0° C., 10.0 g (50.2 mmol) of3-chlorotetrafluoropropionyl chloride—dissolved in 20 ml ofchloroform—were added to a mixture of 3.97 g (50.2 mmol) of pyridine and5.03 g (50.2 mmol) of butyl vinyl ether in 80 ml of chloroform. Afterthe addition, stirring was continued at room temperature for a further15 h. 100 ml of water were then added to the mixture, and the organicphase was separated off, dried and concentrated. This gave 10.4 g (78%of theory) of a yellowish oil.

¹H-NMR: [CDCl₃] 0.96 (t, 3H); 1.43 (m, 2H); 1.75 (m, 2H); 4.04 (t, 2H);5.97 (d, 1H); 7.91 (d, 1H).

A17.2) Methyl6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

0.32 g (13.7 mmol) of sodium were dissolved in 50 ml of methanol, 3.0 g(11.4 mmol) of 1-butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one and1.34 g (11.4 mmol) of methyl malonatemonoamide were added and themixture was heated under reflux for 6 h. The mixture was concentrated toabout 30 ml, 50 ml of 1 N hydrochloric acid were then added and themixture was subsequently extracted repeatedly with ethyl acetate. Afterdrying and concentration, the resulting residue was taken up in diethylether and filtered. Concentration of the filtrate gave 1.74 g (52% oftheory) of a yellowish powder.

¹H-NMR: [DMSO] 3.84 (s, 3H); 7.44 (d, 1H); 8.32 (d, 1H); 12.4 (br, 1H).

A17.3)6-(2-Chloro-1,1,2,2-tetrafluoroethyl)-N-ethyl-2-oxo-1,2-dihydropyridine-3-carboxamide

At room temperature, 300 mg (1.04 mmol) of methyl6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxylatewere stirred in 5 ml of aqueous ethylamine solution (70%) for 14 h. ThepH was then adjusted to 2 by addition of 1 N hydrochloric acid, and themixture was extracted with dichloromethane. Drying and concentration ofthe extract gave 310 mg (98% of theory) of the product.

¹H-NMR: [CDCl₃] 1.27 (t, 3H); 3.50 (m, 2H); 6.88 (d, 1H); 8.68 (d, 1H);9.32 (br, 1H); 12.6 (br, 1H).

Example A18

5-Bromo-6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamideA18.1)6-(2-Chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

0.53 g (22.8 mmol) of sodium were dissolved in 50 ml of methanol, 5.0 g(19.0 mmol) of 1-butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one and2.0 g (19.0 mmol) of malonamide were then added and the mixture washeated under reflux for 6 h. The mixture was concentrated, and 1 Nhydrochloric acid was then added. The resulting precipitate was filteredoff with suction and dried. This gave 3.8 g (73% of theory) of abrownish powder.

¹H-NMR: [DMSO] 7.42 (br, 1H); 8.10 (br, 1H); 8.40 (br, 1H); 8.46 (d,1H), 13.6 (br, 1H).

A18.2)5-Bromo-6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydro-pyridine-3-carboxamide

0.49 g (1.8 mmol) of6-(2-chloro-1,1,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamidewere dissolved in 5 ml of N,N-dimethylformamide, and 0.48 g (2.7 mmol)of N-bromosuccinimide was added at room temperature. After 2 hours ofstirring at room temperature, the reaction mixture was poured intowater, resulting in the formation of a precipitate. Filtration withsuction, washing with water and drying gave 610 mg (96% of theory) ofthe product as a yellowish powder.

¹H-NMR: [DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.61 (s, 1H); 13.7 (br,1H).

Example A19

6-(1-Chloro-1,2,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamideA19.1) 1-Butoxy-4-chloro-4,5,5,5-tetrafluoropent-1-en-3-one

With stirring and at 0° C., 9.59 g (48.2 mmol) of2-chlorotetrafluoropropionyl chloride were added dropwise to a mixtureof 4.19 g (50.0 mmol) of pyridine and 4.83 g (48.2 mmol) of butyl vinylether in 75 ml of dichloromethane. After the addition, stirring wascontinued at room temperature for another 15 h. The mixture was thenwashed with 1 N hydrochloric acid and 2×100 ml of water, and the organicphase was separated off, dried and concentrated. This gave 6.33 g (50%of theory) of a brown oil.

¹H-NMR: [CDCl₃] 0.97 (t, 3H); 1.48 (m, 2H); 1.75 (m, 2H); 4.03 (t, 2H);5.98 (d, 1H); 7.89 (d, 1H).

A19.2)6-(1-Chloro-1,2,2,2-tetrafluoroethyl)-2-oxo-1,2-dihydropyridine-3-carboxamide

0.33 g (14.4 mmol) of sodium were dissolved in 50 ml of methanol, 3.16 g(12.03 mmol) of 1-butoxy-4-chloro-4,5,5,5-tetrafluoropent-1-en-3-one and1.27 g (12.03 mmol) of malonamide were added and the mixture was heatedunder reflux for 7 h. The mixture was concentrated, and 1 N hydrochloricacid was then added. The resulting precipitate was filtered off withsuction and dried. This gave 380 mg (12% of theory) of a yellowishpowder.

¹H-NMR: [DMSO] 7.45 (d, 1H); 8.14 (br, 1H); 8.42 (br, 1H); 8.48 (d, 1H);13.7 (br, 1H).

In an exemplary manner, Table 1 below lists a number of compounds of thegeneral formula (I) which can be obtained in a manner analogous toExamples A1 to A10 above and to the methods mentioned further above.

In the table:

Bu = butyl Et = ethyl Me = methyl Ph = phenyl Pr = propyl s = secondaryi = iso c = cyclo t = tertiary

This applies correspondingly to composite terms such as

iPr=isopropyliBu=isobutylsBu=sec-butyltBu=tert-butylcPr=cyclopropylcPentyl=cyclopentylcHexyl=cyclohexyl

If an alkyl radical is listed in the tables without furtherspecification, the radical in question is the straight-chain alkylradical, i.e., for example, Bu=n-Bu=n-butyl.

In the table, the number indices in the formula are not subscript butarranged in the same line height and font size as the symbols for theatoms.

For example, the formula CF₃ in the table corresponds to the formula CF₃according to the customary notation with subscript index, or the formulaCH₂CH(CH₂CH₃)₂ corresponds to the formula CH₂CH(CH₂CH₃)₂ with subscriptindices.

For some compounds (I) in Table 1, physicochemical data (in general¹H-NMR data) are listed in Table 2. Here, the data are assigned to thecompounds via the example number according to Table 1.

TABLE 1 Compounds of the formula (I) (I)

Ex. R¹ R² R³ R⁴ 1 CF3 H H Me 2 CF3 H H Et 3 CF3 H H Pr 4 CF3 H H iPr 5CF3 H H cPr 6 CF3 H H Bu 7 CF3 H H cBu 8 CF3 H H tBu 9 CF3 H Me Me 10CF3 H Me Et 11 CF3 H Me Bu 12 CF3 H Me Pr 13 CF3 H Me iPr 14 CF3 H Et Et15 CF3 H Et Pr 16 CF3 H Et iPr 17 CF3 H Pr Pr 18 CF3 H H cPentyl 19 CF3H H cHexyl 20 CF3 H H CH2(CH2)3CH3 21 CF3 H H CH2(CH2)4CH3 22 CF3 H HCH2-cPr 23 CF3 H H CH2-CN 24 CF3 H H CH2—C(CH3)3 25 CF3 H H CH2CF2CF3 26CF3 H H CH2CF3 27 CF3 H H CH2(CF2)2CF3 28 CF3 H H CH2CH(CH3)CH2CH3 29CF3 H H CH2C(CH3)2CH2F 30 CF3 H H CH2CH(CH3)2 31 CF3 H H CH2CH(CH2CH3)232 CF3 H H CH2CH2CH(CH3)2 33 CF3 H H CH2CH2C(CH3)3 34 CF3 H H CH2CH═CH235 CF3 H Me CH2CH═CH2 36 CF3 H CH2CH═CH2 CH2CH═CH2 37 CF3 H HCH2CH═CHCH3 38 CF3 H H CH2—C(CH3)═CH2 39 CF3 H H CH2—C≡CH 40 CF3 H MeCH2—C≡CH 41 CF3 H H CH(CH3)CH2CH3 42 CF3 H H CH(CH3)cPr 43 CF3 H HCH(CH3)(CH2)2CH3 44 CF3 H H CH(CH3)(CH2)4CH3 45 CF3 H H CH(CH3)(CH2)5CH346 CF3 H H CH(CH2CH3)(CH2)3CH3 47 CF3 H H CH(CH3)CH2CH(CH3)2 48 CF3 H HCH(CH3)C(CH3)3 49 CF3 H H CH(CH3)CH(CH3)2 50 CF3 H HCH(CH3)CH2CH2CH(CH3)2 51 CF3 H H CH(CH2CH3)2 52 CF3 H H C(CH3)2CH2CH3 53CF3 H H C(CH3)2CH2C(CH3)3 54 CF3 H H CH2—CH(OMe)2 55 CF3 H HCH2—CH(OEt)2 56 CF3 H H CH2CH2—OH 57 CF3 H H CH2CH2-OMe 58 CF3 H MeCH2CH2-OMe 59 CF3 H H CH2CH2-OEt 60 CF3 H H CH2CH2-SMe 61 CF3 H HCH2CH2-CN 62 CF3 H H CH2CH2-NMe2 63 CF3 H H CH2CH2-morpholin-4-yl 64 CF3H H CH(CH3)CH2-OMe 65 CF3 H H CH(CH3)CH2-NMe2 66 CF3 H H CH2CH2CH2-OMe67 CF3 H H CH2CH2CH2-SMe 68 CF3 H H CH2CH2CH2-OEt 69 CF3 H HCH2CH2CH2-OiPr 70 CF3 H H CH2CH2CH2-OBu 71 CF3 H H CH2—COOCH3 72 CF3 HMe CH2—COOCH3 73 CF3 H H CH(CH3)COOMe 74 CF3 H H CH(CH3)COOEt 75 CF3 H HCH2CH2—COOCH3 76 CF3 H H CH(COOCH3)2 77 CF3 H H CH(COOEt)CH2—CH(CH3)2 78CF3 H H CH(COOMe)CH(CH3)2 79 CF3 H H O—CH2CH3 80 CF3 H Me O—CH3 81 CF3 HH O—CH2CH═CH2 82 CF3 H H O-tBu 83 CF3 H H O-Pr 84 CF3 H H O—CH2cPr 85CF3 H H O—CH2CH(CH3)2 86 CF3 H H O—CH2CF3 87 CF3 H H O—CH(CH3)cPr 88 CF3H H O—CH2CH2Cl 89 CF3 H H O—CH2C≡CH 90 CF3 H H O—CH2C≡CCH3 91 CF3 H HO—CH(CH3)C≡CH 92 CF3 H H CH2-Ph 93 CF3 H Me CH2-Ph 94 CF3 H HCH2-pyridin-3-yl 95 CF3 H H CH2-6-Cl-pyridin-3-yl 96 CF3 H H CH(CH3)Ph97 CF3 H H CH2CH2-Ph 98 CF3 H H CH2-2-CF3-Ph 99 CF3 H H CH2CH2CHPh2 100CF3 H morpholin-4-yl 101 CF3 H piperidin-1-yl 102 CF3 H thiazolidin-3-yl103 CF3 H pyrrolidin-1-yl 104 CF3 H 2-methylpyrrolidin-1-yl 105 CF3 H═CH—N(CH3)2 106 CF3 H ═C(CH3)N(CH3)2 107 CF3 H ═CH—N(C2H5)2 108 CF3 H═C(CH3)N(C2H5)2 109 CF3 H ═CH-piperidine 110 CF3 H ═CH-morpholine 111CF3 H ═CH-pyrrolidine 112 CF3 H H indan-1-yl 113 CF3 H Htetrahydrofuran-2-ylmethyl 114 CF2Cl H H H 115 CF2Cl H H Me 116 CF2Cl HH Et 117 CF2Cl H H Pr 118 CF2Cl H H iPr 119 CF2Cl H H cPr 120 CF2Cl H HBu 121 CF2Cl H H cBu 122 CF2Cl H H tBu 123 CF2Cl H Me Me 124 CF2Cl H MeEt 125 CF2Cl H Me Bu 126 CF2Cl H Me Pr 127 CF2Cl H Me iPr 128 CF2Cl H EtEt 129 CF2Cl H Et Pr 130 CF2Cl H Et iPr 131 CF2Cl H Pr Pr 132 CF2Cl H HcPentyl 133 CF2Cl H H cHexyl 134 CF2Cl H H CH2(CH2)3CH3 135 CF2Cl H HCH2(CH2)4CH3 136 CF2Cl H H CH2-cPr 137 CF2Cl H H CH2-CN 138 CF2Cl H HCH2—C(CH3)3 139 CF2Cl H H CH2CF2CF3 140 CF2Cl H H CH2CF3 141 CF2Cl H HCH2(CF2)2CF3 142 CF2Cl H H CH2CH(CH3)CH2CH3 143 CF2Cl H H CH2C(CH3)2CH2F144 CF2Cl H H CH2CH(CH3)2 145 CF2Cl H H CH2CH(CH2CH3)2 146 CF2Cl H HCH2CH2CH(CH3)2 147 CF2Cl H H CH2CH2C(CH3)3 148 CF2Cl H H CH2CH═CH2 149CF2Cl H Me CH2CH═CH2 150 CF2Cl H CH2CH═CH2 CH2CH═CH2 151 CF2Cl H HCH2CH═CHCH3 152 CF2Cl H H CH2—C(CH3)═CH2 153 CF2Cl H H CH2—C≡CH 154CF2Cl H Me CH2—C≡CH 155 CF2Cl H H CH(CH3)CH2CH3 156 CF2Cl H H CH(CH3)cPr157 CF2Cl H H CH(CH3)(CH2)2CH3 158 CF2Cl H H CH(CH3)(CH2)4CH3 159 CF2ClH H CH(CH3)(CH2)5CH3 160 CF2Cl H H CH(CH2CH3)(CH2)3CH3 161 CF2Cl H HCH(CH3)CH2CH(CH3)2 162 CF2Cl H H CH(CH3)C(CH3)3 163 CF2Cl H HCH(CH3)CH(CH3)2 164 CF2Cl H H CH(CH3)CH2CH2CH(CH3)2 165 CF2Cl H HCH(CH2CH3)2 166 CF2Cl H H C(CH3)2CH2CH3 167 CF2Cl H H C(CH3)2CH2C(CH3)3168 CF2Cl H H CH2—CH(OMe)2 169 CF2Cl H H CH2—CH(OEt)2 170 CF2Cl H HCH2CH2—OH 171 CF2Cl H H CH2CH2-OMe 172 CF2Cl H Me CH2CH2-OMe 173 CF2Cl HH CH2CH2-OEt 174 CF2Cl H H CH2CH2-SMe 175 CF2Cl H H CH2CH2-CN 176 CF2ClH H CH2CH2-NMe2 177 CF2Cl H H CH2CH2-morpholin-4-yl 178 CF2Cl H HCH(CH3)CH2-OMe 179 CF2Cl H H CH(CH3)CH2-NMe2 180 CF2Cl H H CH2CH2CH2-OMe181 CF2Cl H H CH2CH2CH2-SMe 182 CF2Cl H H CH2CH2CH2-OEt 183 CF2Cl H HCH2CH2CH2-OiPr 184 CF2Cl H H CH2CH2CH2-OBu 185 CF2Cl H H CH2—COOCH3 186CF2Cl H Me CH2—COOCH3 187 CF2Cl H H CH(CH3)COOMe 188 CF2Cl H HCH(CH3)COOEt 189 CF2Cl H H CH2CH2—COOCH3 190 CF2Cl H H CH(COOCH3)2 191CF2Cl H H CH(COOEt)CH2—CH(CH3)2 192 CF2Cl H H CH(COOMe)CH(CH3)2 193CF2Cl H H O—CH2CH3 194 CF2Cl H H O—CH3 195 CF2Cl H H O—CH2CH═CH2 196CF2Cl H H O-tBu 197 CF2Cl H H O-Pr 198 CF2Cl H H O—CH2cPr 199 CF2Cl H HO—CH2CH(CH3)2 200 CF2Cl H H O—CH2CF3 201 CF2Cl H H O—CH(CH3)cPr 202CF2Cl H H O—CH2CH2Cl 203 CF2Cl H H O—CH2C≡CH 204 CF2Cl H H O—CH2C≡CCH3205 CF2Cl H H O—CH(CH3)C≡CH 206 CF2Cl H H CH2-Ph 207 CF2Cl H Me CH2-Ph208 CF2Cl H H CH2-pyridin-3-yl 209 CF2Cl H H CH2-6-Cl-pyridin-3-yl 210CF2Cl H H CH(CH3)Ph 211 CF2Cl H H CH2CH2-Ph 212 CF2Cl H H CH2-2-CF3-Ph213 CF2Cl H H CH2CH2CHPh 214 CF2Cl H morpholin-4-yl 215 CF2Cl Hpiperidin-1-yl 216 CF2Cl H thiazolidin-3-yl 217 CF2Cl H pyrrolidin-1-yl218 CF2Cl H 2-methylpyrrolidin-1-yl 219 CF2Cl H ═CH—N(CH3)2 220 CF2Cl H═C(CH3)N(CH3)2 221 CF2Cl H ═CH—N(C2H5)2 222 CF2Cl H ═C(CH3)N(C2H5)2 223CF2Cl H ═CH-piperidine 224 CF2Cl H ═CH-morphoilne 225 CF2Cl H═CH-pyrrolidine 226 CF2Cl H H indan-1-yl 227 CF2Cl H Htetrahydrofuran-2-ylmethyl 228 CHF2 H H H 229 CHF2 H H Me 230 CHF2 H HEt 231 CHF2 H H Pr 232 CHF2 H H iPr 233 CHF2 H H cPr 234 CHF2 H H Bu 235CHF2 H H cBu 236 CHF2 H H tBu 237 CHF2 H Me Me 238 CHF2 H Me Et 239 CHF2H Me Bu 240 CHF2 H Me Pr 241 CHF2 H Me iPr 242 CHF2 H Et Et 243 CHF2 HEt Pr 244 CHF2 H Et iPr 245 CHF2 H Pr Pr 246 CHF2 H H cPentyl 247 CHF2 HH cHexyl 248 CHF2 H H CH2(CH2)3CH3 249 CHF2 H H CH2(CH2)4CH3 250 CHF2 HH CH2-cPr 251 CHF2 H H CH2-CN 252 CHF2 H H CH2—C(CH3)3 253 CHF2 H HCH2CF2CF3 254 CHF2 H H CH2CF3 255 CHF2 H H CH2(CF2)2CF3 256 CHF2 H HCH2CH(CH3)CH2CH3 257 CHF2 H H CH2C(CH3)2CH2F 258 CHF2 H H CH2CH(CH3)2259 CHF2 H H CH2CH(CH2CH3)2 260 CHF2 H H CH2CH2CH(CH3)2 261 CHF2 H HCH2CH2C(CH3)3 262 CHF2 H H CH2CH═CH2 263 CHF2 H Me CH2CH═CH2 264 CHF2 HCH2CH═CH2 CH2CH═CH2 265 CHF2 H H CH2CH═CHCH3 266 CHF2 H H CH2—C(CH3)═CH2267 CHF2 H H CH2—C≡CH 268 CHF2 H Me CH2—C≡CH 269 CHF2 H H CH(CH3)CH2CH3270 CHF2 H H CH(CH3)cPr 271 CHF2 H H CH(CH3)(CH2)2CH3 272 CHF2 H HCH(CH3)(CH2)4CH3 273 CHF2 H H CH(CH3)(CH2)5CH3 274 CHF2 H HCH(CH2CH3)(CH2)3CH3 275 CHF2 H H CH(CH3)CH2CH(CH3)2 276 CHF2 H HCH(CH3)C(CH3)3 277 CHF2 H H CH(CH3)CH(CH3)2 278 CHF2 H HCH(CH3)CH2CH2CH(CH3)2 279 CHF2 H H CH(CH2CH3)2 280 CHF2 H HC(CH3)2CH2CH3 281 CHF2 H H C(CH3)2CH2C(CH3)3 282 CHF2 H H CH2—CH(OMe)2283 CHF2 H H CH2—CH(OEt)2 284 CHF2 H H CH2CH2—OH 285 CHF2 H H CH2CH2-OMe286 CHF2 H H CH2CH2-OEt 287 CHF2 H H CH2CH2-SMe 288 CHF2 H H CH2CH2-CN289 CHF2 H H CH2CH2-NMe2 290 CHF2 H H CH2CH2-morpholin-4-yl 291 CHF2 H HCH(CH3)CH2-OMe 292 CHF2 H H CH(CH3)CH2-NMe2 293 CHF2 H H CH2CH2CH2-OMe294 CHF2 H H CH2CH2CH2-SMe 295 CHF2 H H CH2CH2CH2-OEt 296 CHF2 H HCH2CH2CH2-OiPr 297 CHF2 H H CH2CH2CH2-OBu 298 CHF2 H H CH2—COOCH3 299CHF2 H Me CH2—COOCH3 300 CHF2 H H CH(CH3)COOMe 301 CHF2 H H CH(CH3)COOEt302 CHF2 H H CH2CH2—COOCH3 303 CHF2 H H CH(COOCH3)2 304 CHF2 H HCH(COOEt)CH2—CH(CH3)2 305 CHF2 H H CH(COOMe)CH(CH3)2 306 CHF2 H HO—CH2CH3 307 CHF2 H H O—CH3 308 CHF2 H H O—CH2CH═CH2 309 CHF2 H H O-tBu310 CHF2 H H O-Pr 311 CHF2 H H O—CH2cPr 312 CHF2 H H O—CH2CH(CH3)2 313CHF2 H H O—CH2CF3 314 CHF2 H H O—CH(CH3)cPr 315 CHF2 H H O—CH2CH2Cl 316CHF2 H H O—CH2C≡CH 317 CHF2 H H O—CH2C≡CCH3 318 CHF2 H H O—CH(CH3)C≡CH319 CHF2 H H CH2-Ph 320 CHF2 H Me CH2-Ph 321 CHF2 H H CH2-pyridin-3-yl322 CHF2 H H CH2-6-Cl-pyridin-3-yl 323 CHF2 H H CH(CH3)Ph 324 CHF2 H HCH2CH2-Ph 325 CHF2 H H CH2-2-CF3-Ph 326 CHF2 H H CH2CH2CHPh 327 CHF2 Hmorpholin-4-yl 328 CHF2 H piperidin-1-yl 329 CHF2 H thiazolidin-3-yl 330CHF2 H pyrrolidin-1-yl 331 CHF2 H 2-methylpyrrolidin-1-yl 332 CHF2 H═CH—N(CH3)2 333 CHF2 H ═C(CH3)N(CH3)2 334 CHF2 H ═CH—N(C2H5)2 335 CHF2 H═C(CH3)N(C2H5)2 336 CHF2 H ═CH-piperidine 337 CHF2 H ═CH-morpholine 338CHF2 H ═CH-pyrrolidine 339 CHF2 H H indan-1-yl 340 CHF2 H Htetrahydrofuran-2-ylmethyl 341 CF2CF3 H H H 342 CF2CF3 H H Me 343 CF2CF3H H Et 344 CF2CF3 H H Pr 345 CF2CF3 H H iPr 346 CF2CF3 H H cPr 347CF2CF3 H H Bu 348 CF2CF3 H H cBu 349 CF2CF3 H H tBu 350 CF2CF3 H Me Me351 CF2CF3 H Me Et 352 CF2CF3 H Me Bu 353 CF2CF3 H Me Pr 354 CF2CF3 H MeiPr 355 CF2CF3 H Et Et 356 CF2CF3 H Et Pr 357 CF2CF3 H Et iPr 358 CF2CF3H Pr Pr 359 CF2CF3 H H cPentyl 360 CF2CF3 H H cHexyl 361 CF2CF3 H HCH2(CH2)3CH3 362 CF2CF3 H H CH2(CH2)4CH3 363 CF2CF3 H H CH2-cPr 364CF2CF3 H H CH2-CN 365 CF2CF3 H H CH2—C(CH3)3 366 CF2CF3 H H CH2CF2CF3367 CF2CF3 H H CH2CF3 368 CF2CF3 H H CH2(CF2)2CF3 369 CF2CF3 H HCH2CH(CH3)CH2CH3 370 CF2CF3 H H CH2C(CH3)2CH2F 371 CF2CF3 H HCH2CH(CH3)2 372 CF2CF3 H H CH2CH(CH2CH3)2 373 CF2CF3 H H CH2CH2CH(CH3)2374 CF2CF3 H H CH2CH2C(CH3)3 375 CF2CF3 H H CH2CH═CH2 376 CF2CF3 H MeCH2CH═CH2 377 CF2CF3 H CH2CH═CH2 CH2CH═CH2 378 CF2CF3 H H CH2CH═CHCH3379 CF2CF3 H H CH2—C(CH3)═CH2 380 CF2CF3 H H CH2—C≡CH 381 CF2CF3 H MeCH2—C≡CH 382 CF2CF3 H H CH(CH3)CH2CH3 383 CF2CF3 H H CH(CH3)cPr 384CF2CF3 H H CH(CH3)(CH2)2CH3 385 CF2CF3 H H CH(CH3)(CH2)4CH3 386 CF2CF3 HH CH(CH3)(CH2)5CH3 387 CF2CF3 H H CH(CH2CH3)(CH2)3CH3 388 CF2CF3 H HCH(CH3)CH2CH(CH3)2 389 CF2CF3 H H CH(CH3)C(CH3)3 390 CF2CF3 H HCH(CH3)CH(CH3)2 391 CF2CF3 H H CH(CH3)CH2CH2CH(CH3)2 392 CF2CF3 H HCH(CH2CH3)2 393 CF2CF3 H H C(CH3)2CH2CH3 394 CF2CF3 H HC(CH3)2CH2C(CH3)3 395 CF2CF3 H H CH2—CH(OMe)2 396 CF2CF3 H HCH2—CH(OEt)2 397 CF2CF3 H H CH2CH2—OH 398 CF2CF3 H H CH2CH2-OMe 399CF2CF3 H Me CH2CH2-OMe 400 CF2CF3 H H CH2CH2-OEt 401 CF2CF3 H HCH2CH2-SMe 402 CF2CF3 H H CH2CH2-CN 403 CF2CF3 H H CH2CH2-NMe2 404CF2CF3 H H CH2CH2-morpholin-4-yl 405 CF2CF3 H H CH(CH3)CH2-OMe 406CF2CF3 H H CH(CH3)CH2-NMe2 407 CF2CF3 H H CH2CH2CH2-OMe 408 CF2CF3 H HCH2CH2CH2-SMe 409 CF2CF3 H H CH2CH2CH2-OEt 410 CF2CF3 H H CH2CH2CH2-OiPr411 CF2CF3 H H CH2CH2CH2-OBu 412 CF2CF3 H H CH2—COOCH3 413 CF2CF3 H MeCH2—COOCH3 414 CF2CF3 H H CH(CH3)COOMe 415 CF2CF3 H H CH(CH3)COOEt 416CF2CF3 H H CH2CH2—COOCH3 417 CF2CF3 H H CH(COOCH3)2 418 CF2CF3 H HCH(COOEt)CH2—CH(CH3)2 419 CF2CF3 H H CH(COOMe)CH(CH3)2 420 CF2CF3 H HO—CH2CH3 421 CF2CF3 H H O—CH3 422 CF2CF3 H H O—CH2CH═CH2 423 CF2CF3 H HO-tBu 424 CF2CF3 H H O-Pr 425 CF2CF3 H H O—CH2cPr 426 CF2CF3 H HO—CH2CH(CH3)2 427 CF2CF3 H H O—CH2CF3 428 CF2CF3 H H O—CH(CH3)cPr 429CF2CF3 H H O—CH2CH2Cl 430 CF2CF3 H H O—CH2C≡CH 431 CF2CF3 H HO—CH2C≡CCH3 432 CF2CF3 H H O—CH(CH3)C≡CH 433 CF2CF3 H H CH2-Ph 434CF2CF3 H Me CH2-Ph 435 CF2CF3 H H CH2-pyridin-3-yl 436 CF2CF3 H HCH2-6-Cl-pyridin-3-yl 437 CF2CF3 H H CH(CH3)Ph 438 CF2CF3 H H CH2CH2-Ph439 CF2CF3 H H CH2-2-CF3-Ph 440 CF2CF3 H H CH2CH2CHPh 441 CF2CF3 Hmorpholin-4-yl 442 CF2CF3 H piperidin-1-yl 443 CF2CF3 H thiazolidin-3-yl444 CF2CF3 H pyrrolidin-1-yl 445 CF2CF3 H 2-methylpyrrolidin-1-yl 446CF2CF3 H ═CH—N(CH3)2 447 CF2CF3 H ═C(CH3)N(CH3)2 448 CF2CF3 H═CH—N(C2H5)2 449 CF2CF3 H ═C(CH3)N(C2H5)2 450 CF2CF3 H ═CH-piperidine451 CF2CF3 H ═CH-morpholine 452 CF2CF3 H ═CH-pyrrolidine 453 CF2CF3 H Hindan-1-yl 454 CF2CF3 H H tetrahydrofuran-2-ylmethyl 455 CF3 Cl H H 456CF3 Cl H Me 457 CF3 Cl H Et 458 CF3 Cl H Pr 459 CF3 Cl H iPr 460 CF3 ClH cPr 461 CF3 Cl H Bu 462 CF3 Cl H cBu 463 CF3 Cl H tBu 464 CF3 Cl Me Me465 CF3 Cl Me Et 466 CF3 Cl Me Bu 467 CF3 Cl Me Pr 468 CF3 Cl Me iPr 469CF3 Cl Et Et 470 CF3 Cl Et Pr 471 CF3 Cl Et iPr 472 CF3 Cl Pr Pr 473 CF3Cl H cPentyl 474 CF3 Cl H cHexyl 475 CF3 Cl H CH2(CH2)3CH3 476 CF3 Cl HCH2(CH2)4CH3 477 CF3 Cl H CH2-cPr 478 CF3 Cl H CH2-CN 479 CF3 Cl HCH2—C(CH3)3 480 CF3 Cl H CH2CF2CF3 481 CF3 Cl H CH2CF3 482 CF3 Cl HCH2(CF2)2CF3 483 CF3 Cl H CH2CH(CH3)CH2CH3 484 CF3 Cl H CH2C(CH3)2CH2F485 CF3 Cl H CH2CH(CH3)2 486 CF3 Cl H CH2CH(CH2CH3)2 487 CF3 Cl HCH2CH2CH(CH3)2 488 CF3 Cl H CH2CH2C(CH3)3 489 CF3 Cl H CH2CH═CH2 490 CF3Cl Me CH2CH═CH2 491 CF3 Cl CH2CH═CH2 CH2CH═CH2 492 CF3 Cl H CH2CH═CHCH3493 CF3 Cl H CH2—C(CH3)═CH2 494 CF3 Cl H CH2—C≡CH 495 CF3 Cl Me CH2—C≡CH496 CF3 Cl H CH(CH3)CH2CH3 497 CF3 Cl H CH(CH3)cPr 498 CF3 Cl HCH(CH3)(CH2)2CH3 499 CF3 Cl H CH(CH3)(CH2)4CH3 500 CF3 Cl HCH(CH3)(CH2)5CH3 501 CF3 Cl H CH(CH2CH3)(CH2)3CH3 502 CF3 Cl HCH(CH3)CH2CH(CH3)2 503 CF3 Cl H CH(CH3)C(CH3)3 504 CF3 Cl HCH(CH3)CH(CH3)2 505 CF3 Cl H CH(CH3)CH2CH2CH(CH3)2 506 CF3 Cl HCH(CH2CH3)2 507 CF3 Cl H C(CH3)2CH2CH3 508 CF3 Cl H C(CH3)2CH2C(CH3)3509 CF3 Cl H CH2—CH(OMe)2 510 CF3 Cl H CH2—CH(OEt)2 511 CF3 Cl HCH2CH2—OH 512 CF3 Cl H CH2CH2-OMe 513 CF3 Cl Me CH2CH2-OMe 514 CF3 Cl HCH2CH2-OEt 515 CF3 Cl H CH2CH2-SMe 516 CF3 Cl H CH2CH2-CN 517 CF3 Cl HCH2CH2-NMe2 518 CF3 Cl H CH2CH2-morpholin-4-yl 519 CF3 Cl HCH(CH3)CH2-OMe 520 CF3 Cl H CH(CH3)CH2-NMe2 521 CF3 Cl H CH2CH2CH2-OMe522 CF3 Cl H CH2CH2CH2-SMe 523 CF3 Cl H CH2CH2CH2-OEt 524 CF3 Cl HCH2CH2CH2-OiPr 525 CF3 Cl H CH2CH2CH2-OBu 526 CF3 Cl H CH2—COOCH3 527CF3 Cl Me CH2—COOCH3 528 CF3 Cl H CH(CH3)COOMe 529 CF3 Cl H CH(CH3)COOEt530 CF3 Cl H CH2CH2—COOCH3 531 CF3 Cl H CH(COOCH3)2 532 CF3 Cl HCH(COOEt)CH2—CH(CH3)2 533 CF3 Cl H CH(COOMe)CH(CH3)2 534 CF3 Cl HO—CH2CH3 535 CF3 Cl Me O—CH3 536 CF3 Cl H O—CH2CH═CH2 537 CF3 Cl H O-tBu538 CF3 Cl H O-Pr 539 CF3 Cl H O—CH2cPr 540 CF3 Cl H O—CH2CH(CH3)2 541CF3 Cl H O—CH2CF3 542 CF3 Cl H O—CH(CH3)cPr 543 CF3 Cl H O—CH2CH2Cl 544CF3 Cl H O—CH2C≡CH 545 CF3 Cl H O—CH2C≡CCH3 546 CF3 Cl H O—CH(CH3)C≡CH547 CF3 Cl H CH2-Ph 548 CF3 Cl Me CH2-Ph 549 CF3 Cl H CH2-pyridin-3-yl550 CF3 Cl H CH2-6-Cl-pyridin-3-yl 551 CF3 Cl H CH(CH3)Ph 552 CF3 Cl HCH2CH2-Ph 553 CF3 Cl H CH2-2-CF3-Ph 554 CF3 Cl H CH2CH2CHPh2 555 CF3 Clmorpholin-4-yl 556 CF3 Cl piperidin-1-yl 557 CF3 Cl thiazolidin-3-yl 558CF3 Cl pyrrolidin-1-yl 559 CF3 Cl 2-methylpyrrolidin-1-yl 560 CF3 Cl═CH—N(CH3)2 561 CF3 Cl ═C(CH3)N(CH3)2 562 CF3 Cl ═CH—N(C2H5)2 563 CF3 Cl═C(CH3)N(C2H5)2 564 CF3 Cl ═CH-piperidine 565 CF3 Cl ═CH-morpholine 566CF3 Cl ═CH-pyrrolidine 567 CF3 Cl H indan-1-yl 568 CF3 Cl Htetrahydrofuran-2-ylmethyl 569 CF2Cl Cl H H 570 CF2Cl Cl H Me 571 CF2ClCl H Et 572 CF2Cl Cl H Pr 573 CF2Cl Cl H iPr 574 CF2Cl Cl H cPr 575CF2Cl Cl H Bu 576 CF2Cl Cl H cBu 577 CF2Cl Cl H tBu 578 CF2Cl Cl Me Me579 CF2Cl Cl Me Et 580 CF2Cl Cl Me Bu 581 CF2Cl Cl Me Pr 582 CF2Cl Cl MeiPr 583 CF2Cl Cl Et Et 584 CF2Cl Cl Et Pr 585 CF2Cl Cl Et iPr 586 CF2ClCl Pr Pr 587 CF2Cl Cl H cPentyl 588 CF2Cl Cl H cHexyl 589 CF2Cl Cl HCH2(CH2)3CH3 590 CF2Cl Cl H CH2(CH2)4CH3 591 CF2Cl Cl H CH2-cPr 592CF2Cl Cl H CH2-CN 593 CF2Cl Cl H CH2—C(CH3)3 594 CF2Cl Cl H CH2CF2CF3595 CF2Cl Cl H CH2CF3 596 CF2Cl Cl H CH2(CF2)2CF3 597 CF2Cl Cl HCH2CH(CH3)CH2CH3 598 CF2Cl Cl H CH2C(CH3)2CH2F 599 CF2Cl Cl HCH2CH(CH3)2 600 CF2Cl Cl H CH2CH(CH2CH3)2 601 CF2Cl Cl H CH2CH2CH(CH3)2602 CF2Cl Cl H CH2CH2C(CH3)3 603 CF2Cl Cl H CH2CH═CH2 604 CF2Cl Cl MeCH2CH═CH2 605 CF2Cl Cl CH2CH═CH2 CH2CH═CH2 606 CF2Cl Cl H CH2CH═CHCH3607 CF2Cl Cl H CH2—C(CH3)═CH2 608 CF2Cl Cl H CH2—C≡CH 609 CF2Cl Cl MeCH2—C≡CH 610 CF2Cl Cl H CH(CH3)CH2CH3 611 CF2Cl Cl H CH(CH3)cPr 612CF2Cl Cl H CH(CH3)(CH2)2CH3 613 CF2Cl Cl H CH(CH3)(CH2)4CH3 614 CF2Cl ClH CH(CH3)(CH2)5CH3 615 CF2Cl Cl H CH(CH2CH3)(CH2)3CH3 616 CF2Cl Cl HCH(CH3)CH2CH(CH3)2 617 CF2Cl Cl H CH(CH3)C(CH3)3 618 CF2Cl Cl HCH(CH3)CH(CH3)2 619 CF2Cl Cl H CH(CH3)CH2CH2CH(CH3)2 620 CF2Cl Cl HCH(CH2CH3)2 621 CF2Cl Cl H C(CH3)2CH2CH3 622 CF2Cl Cl HC(CH3)2CH2C(CH3)3 623 CF2Cl Cl H CH2—CH(OMe)2 624 CF2Cl Cl HCH2—CH(OEt)2 625 CF2Cl Cl H CH2CH2—OH 626 CF2Cl Cl H CH2CH2-OMe 627CF2Cl Cl Me CH2CH2-OMe 628 CF2Cl Cl H CH2CH2-OEt 629 CF2Cl Cl HCH2CH2-SMe 630 CF2Cl Cl H CH2CH2-CN 631 CF2Cl Cl H CH2CH2-NMe2 632 CF2ClCl H CH2CH2-morpholin-4-yl 633 CF2Cl Cl H CH(CH3)CH2-OMe 634 CF2Cl Cl HCH(CH3)CH2-NMe2 635 CF2Cl Cl H CH2CH2CH2-OMe 636 CF2Cl Cl HCH2CH2CH2-SMe 637 CF2Cl Cl H CH2CH2CH2-OEt 638 CF2Cl Cl H CH2CH2CH2-OiPr639 CF2Cl Cl H CH2CH2CH2-OBu 640 CF2Cl Cl H CH2—COOCH3 641 CF2Cl Cl MeCH2—COOCH3 642 CF2Cl Cl H CH(CH3)COOMe 643 CF2Cl Cl H CH(CH3)COOEt 644CF2Cl Cl H CH2CH2—COOCH3 645 CF2Cl Cl H CH(COOCH3)2 646 CF2Cl Cl HCH(COOEt)CH2—CH(CH3)2 647 CF2Cl Cl H CH(COOMe)CH(CH3)2 648 CF2Cl Cl HO—CH2CH3 649 CF2Cl Cl H O—CH3 650 CF2Cl Cl H O—CH2CH═CH2 651 CF2Cl Cl HO-tBu 652 CF2Cl Cl H O-Pr 653 CF2Cl Cl H O—CH2cPr 654 CF2Cl Cl HO—CH2CH(CH3)2 655 CF2Cl Cl H O—CH2CF3 656 CF2Cl Cl H O—CH(CH3)cPr 657CF2Cl Cl H O—CH2CH2Cl 658 CF2Cl Cl H O—CH2C≡CH 659 CF2Cl Cl HO—CH2C≡CCH3 660 CF2Cl Cl H O—CH(CH3)C≡CH 661 CF2Cl Cl H CH2-Ph 662 CF2ClCl Me CH2-Ph 663 CF2Cl Cl H CH2-pyridin-3-yl 664 CF2Cl Cl HCH2-6-Cl-pyridin-3-yl 665 CF2Cl Cl H CH(CH3)Ph 666 CF2Cl Cl H CH2CH2-Ph667 CF2Cl Cl H CH2-2-CF3-Ph 668 CF2Cl Cl H CH2CH2CHPh 669 CF2Cl Clmorpholin-4-yl 670 CF2Cl Cl piperidin-1-yl 671 CF2Cl Cl thiazolidin-3-yl672 CF2Cl Cl pyrrolidin-1-yl 673 CF2Cl Cl 2-methylpyrrolidin-1-yl 674CF2Cl Cl ═CH—N(CH3)2 675 CF2Cl Cl ═C(CH3)N(CH3)2 676 CF2Cl Cl═CH—N(C2H5)2 677 CF2Cl Cl ═C(CH3)N(C2H5)2 678 CF2Cl Cl ═CH-piperidine679 CF2Cl Cl ═CH-morpholine 680 CF2Cl Cl ═CH-pyrrolidine 681 CF2Cl Cl Hindan-1-yl 682 CF2Cl Cl H tetrahydrofuran-2-ylmethyl 683 CHF2 Cl H H 684CHF2 Cl H Me 685 CHF2 Cl H Et 686 CHF2 Cl H Pr 687 CHF2 Cl H iPr 688CHF2 Cl H cPr 689 CHF2 Cl H Bu 690 CHF2 Cl H cBu 691 CHF2 Cl H tBu 692CHF2 Cl Me Me 693 CHF2 Cl Me Et 694 CHF2 Cl Me Bu 695 CHF2 Cl Me Pr 696CHF2 Cl Me iPr 697 CHF2 Cl Et Et 698 CHF2 Cl Et Pr 699 CHF2 Cl Et iPr700 CHF2 Cl Pr Pr 701 CHF2 Cl H cPentyl 702 CHF2 Cl H cHexyl 703 CHF2 ClH CH2(CH2)3CH3 704 CHF2 Cl H CH2(CH2)4CH3 705 CHF2 Cl H CH2-cPr 706 CHF2Cl H CH2-CN 707 CHF2 Cl H CH2—C(CH3)3 708 CHF2 Cl H CH2CF2CF3 709 CHF2Cl H CH2CF3 710 CHF2 Cl H CH2(CF2)2CF3 711 CHF2 Cl H CH2CH(CH3)CH2CH3712 CHF2 Cl H CH2C(CH3)2CH2F 713 CHF2 Cl H CH2CH(CH3)2 714 CHF2 Cl HCH2CH(CH2CH3)2 715 CHF2 Cl H CH2CH2CH(CH3)2 716 CHF2 Cl H CH2CH2C(CH3)3717 CHF2 Cl H CH2CH═CH2 718 CHF2 Cl Me CH2CH═CH2 719 CHF2 Cl CH2CH═CH2CH2CH═CH2 720 CHF2 Cl H CH2CH═CHCH3 721 CHF2 Cl H CH2—C(CH3)═CH2 722CHF2 Cl H CH2—C≡CH 723 CHF2 Cl Me CH2—C≡CH 724 CHF2 Cl H CH(CH3)CH2CH3725 CHF2 Cl H CH(CH3)cPr 726 CHF2 Cl H CH(CH3)(CH2)2CH3 727 CHF2 Cl HCH(CH3)(CH2)4CH3 728 CHF2 Cl H CH(CH3)(CH2)5CH3 729 CHF2 Cl HCH(CH2CH3)(CH2)3CH3 730 CHF2 Cl H CH(CH3)CH2CH(CH3)2 731 CHF2 Cl HCH(CH3)C(CH3)3 732 CHF2 Cl H CH(CH3)CH(CH3)2 733 CHF2 Cl HCH(CH3)CH2CH2CH(CH3)2 734 CHF2 Cl H CH(CH2CH3)2 735 CHF2 Cl HC(CH3)2CH2CH3 736 CHF2 Cl H C(CH3)2CH2C(CH3)3 737 CHF2 Cl H CH2—CH(OMe)2738 CHF2 Cl H CH2—CH(OEt)2 739 CHF2 Cl H CH2CH2—OH 740 CHF2 Cl HCH2CH2-OMe 741 CHF2 Cl Me CH2CH2-OMe 742 CHF2 Cl H CH2CH2-OEt 743 CHF2Cl H CH2CH2-SMe 744 CHF2 Cl H CH2CH2-CN 745 CHF2 Cl H CH2CH2-NMe2 746CHF2 Cl H CH2CH2-morpholin-4-yl 747 CHF2 Cl H CH(CH3)CH2-OMe 748 CHF2 ClH CH(CH3)CH2-NMe2 749 CHF2 Cl H CH2CH2CH2-OMe 750 CHF2 Cl HCH2CH2CH2-SMe 751 CHF2 Cl H CH2CH2CH2-OEt 752 CHF2 Cl H CH2CH2CH2-OiPr753 CHF2 Cl H CH2CH2CH2-OBu 754 CHF2 Cl H CH2—COOCH3 755 CHF2 Cl MeCH2—COOCH3 756 CHF2 Cl H CH(CH3)COOMe 757 CHF2 Cl H CH(CH3)COOEt 758CHF2 Cl H CH2CH2—COOCH3 759 CHF2 Cl H CH(COOCH3)2 760 CHF2 Cl HCH(COOEt)CH2—CH(CH3)2 761 CHF2 Cl H CH(COOMe)CH(CH3)2 762 CHF2 Cl HO—CH2CH3 763 CHF2 Cl H O—CH3 764 CHF2 Cl H O—CH2CH═CH2 765 CHF2 Cl HO-tBu 766 CHF2 Cl H O-Pr 767 CHF2 Cl H O—CH2cPr 768 CHF2 Cl HO—CH2CH(CH3)2 769 CHF2 Cl H O—CH2CF3 770 CHF2 Cl H O—CH(CH3)cPr 771 CHF2Cl H O—CH2CH2Cl 772 CHF2 Cl H O—CH2C≡CH 773 CHF2 Cl H O—CH2C≡CCH3 774CHF2 Cl H O—CH(CH3)C≡CH 775 CHF2 Cl H CH2-Ph 776 CHF2 Cl Me CH2-Ph 777CHF2 Cl H CH2-pyridin-3-yl 778 CHF2 Cl H CH2-6-Cl-pyridin-3-yl 779 CHF2Cl H CH(CH3)Ph 780 CHF2 Cl H CH2CH2-Ph 781 CHF2 Cl H CH2-2-CF3-Ph 782CHF2 Cl H CH2CH2CHPh 783 CHF2 Cl morpholin-4-yl 784 CHF2 Clpiperidin-1-yl 785 CHF2 Cl thiazolidin-3-yl 786 CHF2 Cl pyrrolidin-1-yl787 CHF2 Cl 2-methylpyrrolidin-1-yl 788 CHF2 Cl ═CH—N(CH3)2 789 CHF2 Cl═C(CH3)N(CH3)2 790 CHF2 Cl ═CH—N(C2H5)2 791 CHF2 Cl ═C(CH3)N(C2H5)2 792CHF2 Cl ═CH-piperidine 793 CHF2 Cl ═CH-morpholine 794 CHF2 Cl═CH-pyrrolidine 795 CHF2 Cl H indan-1-yl 796 CHF2 Cl Htetrahydrofuran-2-ylmethyl 797 CF2CF3 Cl H H 798 CF2CF3 Cl H Me 799CF2CF3 Cl H Et 800 CF2CF3 Cl H Pr 801 CF2CF3 Cl H iPr 802 CF2CF3 Cl HcPr 803 CF2CF3 Cl H Bu 804 CF2CF3 Cl H cBu 805 CF2CF3 Cl H tBu 806CF2CF3 Cl Me Me 807 CF2CF3 Cl Me Et 808 CF2CF3 Cl Me Bu 809 CF2CF3 Cl MePr 810 CF2CF3 Cl Me iPr 811 CF2CF3 Cl Et Et 812 CF2CF3 Cl Et Pr 813CF2CF3 Cl Et iPr 814 CF2CF3 Cl Pr Pr 815 CF2CF3 Cl H cPentyl 816 CF2CF3Cl H cHexyl 817 CF2CF3 Cl H CH2(CH2)3CH3 818 CF2CF3 Cl H CH2(CH2)4CH3819 CF2CF3 Cl H CH2-cPr 820 CF2CF3 Cl H CH2-CN 821 CF2CF3 Cl HCH2—C(CH3)3 822 CF2CF3 Cl H CH2CF2CF3 823 CF2CF3 Cl H CH2CF3 824 CF2CF3Cl H CH2(CF2)2CF3 825 CF2CF3 Cl H CH2CH(CH3)CH2CH3 826 CF2CF3 Cl HCH2C(CH3)2CH2F 827 CF2CF3 Cl H CH2CH(CH3)2 828 CF2CF3 Cl HCH2CH(CH2CH3)2 829 CF2CF3 Cl H CH2CH2CH(CH3)2 830 CF2CF3 Cl HCH2CH2C(CH3)3 831 CF2CF3 Cl H CH2CH═CH2 832 CF2CF3 Cl Me CH2CH═CH2 833CF2CF3 Cl CH2CH═CH2 CH2CH═CH2 834 CF2CF3 Cl H CH2CH═CHCH3 835 CF2CF3 ClH CH2—C(CH3)═CH2 836 CF2CF3 Cl H CH2—C≡CH 837 CF2CF3 Cl Me CH2—C≡CH 838CF2CF3 Cl H CH(CH3)CH2CH3 839 CF2CF3 Cl H CH(CH3)cPr 840 CF2CF3 Cl HCH(CH3)(CH2)2CH3 841 CF2CF3 Cl H CH(CH3)(CH2)4CH3 842 CF2CF3 Cl HCH(CH3)(CH2)5CH3 843 CF2CF3 Cl H CH(CH2CH3)(CH2)3CH3 844 CF2CF3 Cl HCH(CH3)CH2CH(CH3)2 845 CF2CF3 Cl H CH(CH3)C(CH3)3 846 CF2CF3 Cl HCH(CH3)CH(CH3)2 847 CF2CF3 Cl H CH(CH3)CH2CH2CH(CH3)2 848 CF2CF3 Cl HCH(CH2CH3)2 849 CF2CF3 Cl H C(CH3)2CH2CH3 850 CF2CF3 Cl HC(CH3)2CH2C(CH3)3 851 CF2CF3 Cl H CH2—CH(OMe)2 852 CF2CF3 Cl HCH2—CH(OEt)2 853 CF2CF3 Cl H CH2CH2—OH 854 CF2CF3 Cl H CH2CH2-OMe 855CF2CF3 Cl Me CH2CH2-OMe 856 CF2CF3 Cl H CH2CH2-OEt 857 CF2CF3 Cl HCH2CH2-SMe 858 CF2CF3 Cl H CH2CH2-CN 859 CF2CF3 Cl H CH2CH2-NMe2 860CF2CF3 Cl H CH2CH2-morpholin-4-yl 861 CF2CF3 Cl H CH(CH3)CH2-OMe 862CF2CF3 Cl H CH(CH3)CH2-NMe2 863 CF2CF3 Cl H CH2CH2CH2-OMe 864 CF2CF3 ClH CH2CH2CH2-SMe 865 CF2CF3 Cl H CH2CH2CH2-OEt 866 CF2CF3 Cl HCH2CH2CH2-OiPr 867 CF2CF3 Cl H CH2CH2CH2-OBu 868 CF2CF3 Cl H CH2—COOCH3869 CF2CF3 Cl Me CH2—COOCH3 870 CF2CF3 Cl H CH2CH2—COOCH3 871 CF2CF3 ClH CH(COOCH3)2 872 CF2CF3 Cl H CH(COOEt)CH2—CH(CH3)2 873 CF2CF3 Cl HCH(COOMe)CH(CH3)2 874 CF2CF3 Cl H O—CH2CH3 875 CF2CF3 Cl H O—CH3 876CF2CF3 Cl H O—CH2CH═CH2 877 CF2CF3 Cl H O-tBu 878 CF2CF3 Cl H O-Pr 879CF2CF3 Cl H O—CH2cPr 880 CF2CF3 Cl H O—CH2CH(CH3)2 881 CF2CF3 Cl HO—CH2CF3 882 CF2CF3 Cl H O—CH(CH3)cPr 883 CF2CF3 Cl H O—CH2CH2Cl 884CF2CF3 Cl H O—CH2C≡CH 885 CF2CF3 Cl H O—CH2C≡CCH3 886 CF2CF3 Cl HO—CH(CH3)C≡CH 887 CF2CF3 Cl H CH2-Ph 888 CF2CF3 Cl Me CH2-Ph 889 CF2CF3Cl H CH2-pyridin-3-yl 890 CF2CF3 Cl H CH2-6-Cl-pyridin-3-yl 891 CF2CF3Cl H CH(CH3)Ph 892 CF2CF3 Cl H CH2CH2-Ph 893 CF2CF3 Cl H CH2-2-CF3-Ph894 CF2CF3 Cl H CH2CH2CHPh 895 CF2CF3 Cl morpholin-4-yl 896 CF2CF3 Clpiperidin-1-yl 897 CF2CF3 Cl thiazolidin-3-yl 898 CF2CF3 Clpyrrolidin-1-yl 899 CF2CF3 Cl 2-methylpyrrolidin-1-yl 900 CF2CF3 Cl═CH—N(CH3)2 901 CF2CF3 Cl ═C(CH3)N(CH3)2 902 CF2CF3 Cl ═CH—N(C2H5)2 903CF2CF3 Cl ═C(CH3)N(C2H5)2 904 CF2CF3 Cl ═CH-piperidine 905 CF2CF3 Cl═CH-morpholine 906 CF2CF3 Cl ═CH-pyrrolidine 907 CF2CF3 Cl H indan-1-yl908 CF2CF3 Cl H tetrahydrofuran-2-ylmethyl 909 CF3 Br H H 910 CF3 Br HMe 911 CF3 Br H Et 912 CF3 Br H Pr 913 CF3 Br H iPr 914 CF3 Br H cPr 915CF3 Br H Bu 916 CF3 Br H cBu 917 CF3 Br H tBu 918 CF3 Br Me Me 919 CF3Br Me Et 920 CF3 Br Me Bu 921 CF3 Br Me Pr 922 CF3 Br Me iPr 923 CF3 BrEt Et 924 CF3 Br Et Pr 925 CF3 Br Et iPr 926 CF3 Br Pr Pr 927 CF3 Br HcPentyl 928 CF3 Br H cHexyl 929 CF3 Br H CH2(CH2)3CH3 930 CF3 Br HCH2(CH2)4CH3 931 CF3 Br H CH2-cPr 932 CF3 Br H CH2-CN 933 CF3 Br HCH2—C(CH3)3 934 CF3 Br H CH2CF2CF3 935 CF3 Br H CH2CF3 936 CF3 Br HCH2(CF2)2CF3 937 CF3 Br H CH2CH(CH3)CH2CH3 938 CF3 Br H CH2C(CH3)2CH2F939 CF3 Br H CH2CH(CH3)2 940 CF3 Br H CH2CH(CH2CH3)2 941 CF3 Br HCH2CH2CH(CH3)2 942 CF3 Br H CH2CH2C(CH3)3 943 CF3 Br H CH2CH═CH2 944 CF3Br Me CH2CH═CH2 945 CF3 Br CH2CH═CH2 CH2CH═CH2 946 CF3 Br H CH2CH═CHCH3947 CF3 Br H CH2—C(CH3)═CH2 948 CF3 Br H CH2—C≡CH 949 CF3 Br Me CH2—C≡CH950 CF3 Br H CH(CH3)CH2CH3 951 CF3 Br H CH(CH3)cPr 952 CF3 Br HCH(CH3)(CH2)2CH3 953 CF3 Br H CH(CH3)(CH2)4CH3 954 CF3 Br HCH(CH3)(CH2)5CH3 955 CF3 Br H CH(CH2CH3)(CH2)3CH3 956 CF3 Br HCH(CH3)CH2CH(CH3)2 957 CF3 Br H CH(CH3)C(CH3)3 958 CF3 Br HCH(CH3)CH(CH3)2 959 CF3 Br H CH(CH3)CH2CH2CH(CH3)2 960 CF3 Br HCH(CH2CH3)2 961 CF3 Br H C(CH3)2CH2CH3 962 CF3 Br H C(CH3)2CH2C(CH3)3963 CF3 Br H CH2—CH(OMe)2 964 CF3 Br H CH2—CH(OEt)2 965 CF3 Br HCH2CH2—OH 966 CF3 Br H CH2CH2-OMe 967 CF3 Br Me CH2CH2-OMe 968 CF3 Br HCH2CH2-OEt 969 CF3 Br H CH2CH2-SMe 970 CF3 Br H CH2CH2-CN 971 CF3 Br HCH2CH2-NMe2 972 CF3 Br H CH2CH2-morpholin-4-yl 973 CF3 Br HCH(CH3)CH2-OMe 974 CF3 Br H CH(CH3)CH2-NMe2 975 CF3 Br H CH2CH2CH2-OMe976 CF3 Br H CH2CH2CH2-SMe 977 CF3 Br H CH2CH2CH2-OEt 978 CF3 Br HCH2CH2CH2-OiPr 979 CF3 Br H CH2CH2CH2-OBu 980 CF3 Br H CH2—COOCH3 981CF3 Br Me CH2—COOCH3 982 CF3 Br H CH(CH3)COOMe 983 CF3 Br H CH(CH3)COOEt984 CF3 Br H CH2CH2—COOCH3 985 CF3 Br H CH(COOCH3)2 986 CF3 Br HCH(COOEt)CH2—CH(CH3)2 987 CF3 Br H CH(COOMe)CH(CH3)2 988 CF3 Br HO—CH2CH3 989 CF3 Br Me O—CH3 990 CF3 Br H O—CH2CH═CH2 991 CF3 Br H O-tBu992 CF3 Br H O-Pr 993 CF3 Br H O—CH2cPr 994 CF3 Br H O—CH2CH(CH3)2 995CF3 Br H O—CH2CF3 996 CF3 Br H O—CH(CH3)cPr 997 CF3 Br H O—CH2CH2Cl 998CF3 Br H O—CH2C≡CH 999 CF3 Br H O—CH2C≡CCH3 1000 CF3 Br H O—CH(CH3)C≡CH1001 CF3 Br H CH2-Ph 1002 CF3 Br Me CH2-Ph 1003 CF3 Br HCH2-pyridin-3-yl 1004 CF3 Br H CH2-6-Cl-pyridin-3-yl 1005 CF3 Br HCH(CH3)Ph 1006 CF3 Br H CH2CH2-Ph 1007 CF3 Br H CH2-2-CF3-Ph 1008 CF3 BrH CH2CH2CHPh2 1009 CF3 Br morpholin-4-yl 1010 CF3 Br piperidin-1-yl 1011CF3 Br thiazolidin-3-yl 1012 CF3 Br pyrrolidin-1-yl 1013 CF3 Br2-methylpyrrolidin-1-yl 1014 CF3 Br ═CH—N(CH3)2 1015 CF3 Br═C(CH3)N(CH3)2 1016 CF3 Br ═CH—N(C2H5)2 1017 CF3 Br ═C(CH3)N(C2H5)2 1018CF3 Br ═CH-piperidine 1019 CF3 Br ═CH-morpholine 1020 CF3 Br═CH-pyrroiidine 1021 CF3 Br H indan-1-yl 1022 CF3 Br Htetrahydrofuran-2-ylmethyl 1023 CF2Cl Br H H 1024 CF2Cl Br H Me 1025CF2Cl Br H Et 1026 CF2Cl Br H Pr 1027 CF2Cl Br H iPr 1028 CF2Cl Br H cPr1029 CF2Cl Br H Bu 1030 CF2Cl Br H cBu 1031 CF2Cl Br H tBu 1032 CF2Cl BrMe Me 1033 CF2Cl Br Me Et 1034 CF2Cl Br Me Bu 1035 CF2Cl Br Me Pr 1036CF2Cl Br Me iPr 1037 CF2Cl Br Et Et 1038 CF2Cl Br Et Pr 1039 CF2Cl Br EtiPr 1040 CF2Cl Br Pr Pr 1041 CF2Cl Br H cPentyl 1042 CF2Cl Br H cHexyl1043 CF2Cl Br H CH2(CH2)3CH3 1044 CF2Cl Br H CH2(CH2)4CH3 1045 CF2Cl BrH CH2-cPr 1046 CF2Cl Br H CH2-CN 1047 CF2Cl Br H CH2—C(CH3)3 1048 CF2ClBr H CH2CF2CF3 1049 CF2Cl Br H CH2CF3 1050 CF2Cl Br H CH2(CF2)2CF3 1051CF2Cl Br H CH2CH(CH3)CH2CH3 1052 CF2Cl Br H CH2C(CH3)2CH2F 1053 CF2Cl BrH CH2CH(CH3)2 1054 CF2Cl Br H CH2CH(CH2CH3)2 1055 CF2Cl Br HCH2CH2CH(CH3)2 1056 CF2Cl Br H CH2CH2C(CH3)3 1057 CF2Cl Br H CH2CH═CH21058 CF2Cl Br Me CH2CH═CH2 1059 CF2Cl Br CH2CH═CH2 CH2CH═CH2 1060 CF2ClBr H CH2CH═CHCH3 1061 CF2Cl Br H CH2—C(CH3)═CH2 1062 CF2Cl Br H CH2—C≡CH1063 CF2Cl Br Me CH2—C≡CH 1064 CF2Cl Br H CH(CH3)CH2CH3 1065 CF2Cl Br HCH(CH3)cPr 1066 CF2Cl Br H CH(CH3)(CH2)2CH3 1067 CF2Cl Br HCH(CH3)(CH2)4CH3 1068 CF2Cl Br H CH(CH3)(CH2)5CH3 1069 CF2Cl Br HCH(CH2CH3)(CH2)3CH3 1070 CF2Cl Br H CH(CH3)CH2CH(CH3)2 1071 CF2Cl Br HCH(CH3)C(CH3)3 1072 CF2Cl Br H CH(CH3)CH(CH3)2 1073 CF2Cl Br HCH(CH3)CH2CH2CH(CH3)2 1074 CF2Cl Br H CH(CH2CH3)2 1075 CF2Cl Br HC(CH3)2CH2CH3 1076 CF2Cl Br H C(CH3)2CH2C(CH3)3 1077 CF2Cl Br HCH2—CH(OMe)2 1078 CF2Cl Br H CH2—CH(OEt)2 1079 CF2Cl Br H CH2CH2—OH 1080CF2Cl Br H CH2CH2-OMe 1081 CF2Cl Br Me CH2CH2-OMe 1082 CF2Cl Br HCH2CH2-OEt 1083 CF2Cl Br H CH2CH2-SMe 1084 CF2Cl Br H CH2CH2-CN 1085CF2Cl Br H CH2CH2-NMe2 1086 CF2Cl Br H CH2CH2-morpholin-4-yl 1087 CF2ClBr H CH(CH3)CH2-OMe 1088 CF2Cl Br H CH(CH3)CH2-NMe2 1089 CF2Cl Br HCH2CH2CH2-OMe 1090 CF2Cl Br H CH2CH2CH2-SMe 1091 CF2Cl Br HCH2CH2CH2-OEt 1092 CF2Cl Br H CH2CH2CH2-OiPr 1093 CF2Cl Br HCH2CH2CH2-OBu 1094 CF2Cl Br H CH2—COOCH3 1095 CF2Cl Br Me CH2—COOCH31096 CF2Cl Br H CH(CH3)COOMe 1097 CF2Cl Br H CH(CH3)COOEt 1098 CF2Cl BrH CH2CH2—COOCH3 1099 CF2Cl Br H CH(COOCH3)2 1100 CF2Cl Br HCH(COOEt)CH2—CH(CH3)2 1101 CF2Cl Br H CH(COOMe)CH(CH3)2 1102 CF2Cl Br HO—CH2CH3 1103 CF2Cl Br Me O—CH3 1104 CF2Cl Br H O—CH2CH═CH2 1105 CF2ClBr H O-tBu 1106 CF2Cl Br H O-Pr 1107 CF2Cl Br H O—CH2cPr 1108 CF2Cl Br HO—CH2CH(CH3)2 1109 CF2Cl Br H O—CH2CF3 1110 CF2Cl Br H O—CH(CH3)cPr 1111CF2Cl Br H O—CH2CH2Cl 1112 CF2Cl Br H O—CH2C≡CH 1113 CF2Cl Br HO—CH2C≡CCH3 1114 CF2Cl Br H O—CH(CH3)C≡CH 1115 CF2Cl Br H CH2-Ph 1116CF2Cl Br Me CH2-Ph 1117 CF2Cl Br H CH2-pyridin-3-yl 1118 CF2Cl Br HCH2-6-Cl-pyridin-3-yl 1119 CF2Cl Br H CH(CH3)Ph 1120 CF2Cl Br HCH2CH2-Ph 1121 CF2Cl Br H CH2-2-CF3-Ph 1122 CF2Cl Br H CH2CH2CHPh2 1123CF2Cl Br morpholin-4-yl 1124 CF2Cl Br piperidin-1-yl 1125 CF2Cl Brthiazolidin-3-yl 1126 CF2Cl Br pyrrolidin-1-yl 1127 CF2Cl Br2-methylpyrrolidin-1-yl 1128 CF2Cl Br ═CH—N(CH3)2 1129 CF2Cl Br═C(CH3)N(CH3)2 1130 CF2Cl Br ═CH—N(C2H5)2 1131 CF2Cl Br ═C(CH3)N(C2H5)21132 CF2Cl Br ═CH-piperidine 1133 CF2Cl Br ═CH-morpholine 1134 CF2Cl Br═CH-pyrrolidine 1135 CF2Cl Br H indan-1-yl 1136 CF2Cl Br Htetrahydrofuran-2-ylmethyl 1137 CHF2 Br H H 1138 CHF2 Br H Me 1139 CHF2Br H Et 1140 CHF2 Br H Pr 1141 CHF2 Br H iPr 1142 CHF2 Br H cPr 1143CHF2 Br H Bu 1144 CHF2 Br H cBu 1145 CHF2 Br H tBu 1146 CHF2 Br Me Me1147 CHF2 Br Me Et 1148 CHF2 Br Me Bu 1149 CHF2 Br Me Pr 1150 CHF2 Br MeiPr 1151 CHF2 Br Et Et 1152 CHF2 Br Et Pr 1153 CHF2 Br Et iPr 1154 CHF2Br Pr Pr 1155 CHF2 Br H cPentyl 1156 CHF2 Br H cHexyl 1157 CHF2 Br HCH2(CH2)3CH3 1158 CHF2 Br H CH2(CH2)4CH3 1159 CHF2 Br H CH2-cPr 1160CHF2 Br H CH2-CN 1161 CHF2 Br H CH2—C(CH3)3 1162 CHF2 Br H CH2CF2CF31163 CHF2 Br H CH2CF3 1164 CHF2 Br H CH2(CF2)2CF3 1165 CHF2 Br HCH2CH(CH3)CH2CH3 1166 CHF2 Br H CH2C(CH3)2CH2F 1167 CHF2 Br HCH2CH(CH3)2 1168 CHF2 Br H CH2CH(CH2CH3)2 1169 CHF2 Br H CH2CH2CH(CH3)21170 CHF2 Br H CH2CH2C(CH3)3 1171 CHF2 Br H CH2CH═CH2 1172 CHF2 Br MeCH2CH═CH2 1173 CHF2 Br CH2CH═CH2 CH2CH═CH2 1174 CHF2 Br H CH2CH═CHCH31175 CHF2 Br H CH2—C(CH3)═CH2 1176 CHF2 Br H CH2—C≡CH 1177 CHF2 Br MeCH2—C≡CH 1178 CHF2 Br H CH(CH3)CH2CH3 1179 CHF2 Br H CH(CH3)cPr 1180CHF2 Br H CH(CH3)(CH2)2CH3 1181 CHF2 Br H CH(CH3)(CH2)4CH3 1182 CHF2 BrH CH(CH3)(CH2)5CH3 1183 CHF2 Br H CH(CH2CH3)(CH2)3CH3 1184 CHF2 Br HCH(CH3)CH2CH(CH3)2 1185 CHF2 Br H CH(CH3)C(CH3)3 1186 CHF2 Br HCH(CH3)CH(CH3)2 1187 CHF2 Br H CH(CH3)CH2CH2CH(CH3)2 1188 CHF2 Br HCH(CH2CH3)2 1189 CHF2 Br H C(CH3)2CH2CH3 1190 CHF2 Br HC(CH3)2CH2C(CH3)3 1191 CHF2 Br H CH2—CH(OMe)2 1192 CHF2 Br HCH2—CH(OEt)2 1193 CHF2 Br H CH2CH2—OH 1194 CHF2 Br H CH2CH2-OMe 1195CHF2 Br Me CH2CH2-OMe 1196 CHF2 Br H CH2CH2-OEt 1197 CHF2 Br HCH2CH2-SMe 1198 CHF2 Br H CH2CH2-CN 1199 CHF2 Br H CH2CH2-NMe2 1200 CHF2Br H CH2CH2-morpholin-4-yl 1201 CHF2 Br H CH(CH3)CH2-OMe 1202 CHF2 Br HCH(CH3)CH2-NMe2 1203 CHF2 Br H CH2CH2CH2-OMe 1204 CHF2 Br HCH2CH2CH2-SMe 1205 CHF2 Br H CH2CH2CH2-OEt 1206 CHF2 Br H CH2CH2CH2-OiPr1207 CHF2 Br H CH2CH2CH2-OBu 1208 CHF2 Br H CH2—COOCH3 1209 CHF2 Br MeCH2—COOCH3 1210 CHF2 Br H CH(CH3)COOMe 1211 CHF2 Br H CH(CH3)COOEt 1212CHF2 Br H CH2CH2—COOCH3 1213 CHF2 Br H CH(COOCH3)2 1214 CHF2 Br HCH(COOEt)CH2—CH(CH3)2 1215 CHF2 Br H CH(COOMe)CH(CH3)2 1216 CHF2 Br HO—CH2CH3 1217 CHF2 Br Me O—CH3 1218 CHF2 Br H O—CH2CH═CH2 1219 CHF2 Br HO-tBu 1220 CHF2 Br H O-Pr 1221 CHF2 Br H O—CH2cPr 1222 CHF2 Br HO—CH2CH(CH3)2 1223 CHF2 Br H O—CH2CF3 1224 CHF2 Br H O—CH(CH3)cPr 1225CHF2 Br H O—CH2CH2Cl 1226 CHF2 Br H O—CH2C≡CH 1227 CHF2 Br H O—CH2C≡CCH31228 CHF2 Br H O—CH(CH3)C≡CH 1229 CHF2 Br H CH2-Ph 1230 CHF2 Br MeCH2-Ph 1231 CHF2 Br H CH2-pyridin-3-yl 1232 CHF2 Br HCH2-6-Cl-pyridin-3-yl 1233 CHF2 Br H CH(CH3)Ph 1234 CHF2 Br H CH2CH2-Ph1235 CHF2 Br H CH2-2-CF3-Ph 1236 CHF2 Br H CH2CH2CHPh2 1237 CHF2 Brmorpholin-4-yl 1238 CHF2 Br piperidin-1-yl 1239 CHF2 Br thiazolidin-3-yl1240 CHF2 Br pyrrolidin-1-yl 1241 CHF2 Br 2-methylpyrrolidin-1-yl 1242CHF2 Br ═CH—N(CH3)2 1243 CHF2 Br ═C(CH3)N(CH3)2 1244 CHF2 Br═CH—N(C2H5)2 1245 CHF2 Br ═(CH3)N(C2H5)2 1246 CHF2 Br ═CH-piperidine1247 CHF2 Br ═CH-morpholine 1248 CHF2 Br ═CH-pyrrolidine 1249 CHF2 Br Hindan-1-yl 1250 CHF2 Br H tetrahydrofuran-2-ylmethyl 1251 CF2CF3 Br H H1252 CF2CF3 Br H Me 1253 CF2CF3 Br H Et 1254 CF2CF3 Br H Pr 1255 CF2CF3Br H iPr 1256 CF2CF3 Br H cPr 1257 CF2CF3 Br H Bu 1258 CF2CF3 Br H cBu1259 CF2CF3 Br H tBu 1260 CF2CF3 Br Me Me 1261 CF2CF3 Br Me Et 1262CF2CF3 Br Me Bu 1263 CF2CF3 Br Me Pr 1264 CF2CF3 Br Me iPr 1265 CF2CF3Br Et Et 1266 CF2CF3 Br Et Pr 1267 CF2CF3 Br Et iPr 1268 CF2CF3 Br Pr Pr1269 CF2CF3 Br H cPentyl 1270 CF2CF3 Br H cHexyl 1271 CF2CF3 Br HCH2(CH2)3CH3 1272 CF2CF3 Br H CH2(CH2)4CH3 1273 CF2CF3 Br H CH2-cPr 1274CF2CF3 Br H CH2-CN 1275 CF2CF3 Br H CH2—C(CH3)3 1276 CF2CF3 Br HCH2CF2CF3 1277 CF2CF3 Br H CH2CF3 1278 CF2CF3 Br H CH2(CF2)2CF3 1279CF2CF3 Br H CH2CH(CH3)CH2CH3 1280 CF2CF3 Br H CH2C(CH3)2CH2F 1281 CF2CF3Br H CH2CH(CH3)2 1282 CF2CF3 Br H CH2CH(CH2CH3)2 1283 CF2CF3 Br HCH2CH2CH(CH3)2 1284 CF2CF3 Br H CH2CH2C(CH3)3 1285 CF2CF3 Br H CH2CH═CH21286 CF2CF3 Br Me CH2CH═CH2 1287 CF2CF3 Br CH2CH═CH2 CH2CH═CH2 1288CF2CF3 Br H CH2CH═CHCH3 1289 CF2CF3 Br H CH2—C(CH3)═CH2 1290 CF2CF3 Br HCH2—C≡CH 1291 CF2CF3 Br Me CH2—C≡CH 1292 CF2CF3 Br H CH(CH3)CH2CH3 1293CF2CF3 Br H CH(CH3)cPr 1294 CF2CF3 Br H CH(CH3)(CH2)2CH3 1295 CF2CF3 BrH CH(CH3)(CH2)4CH3 1296 CF2CF3 Br H CH(CH3)(CH2)5CH3 1297 CF2CF3 Br HCH(CH2CH3)(CH2)3CH3 1298 CF2CF3 Br H CH(CH3)CH2CH(CH3)2 1299 CF2CF3 Br HCH(CH3)C(CH3)3 1300 CF2CF3 Br H CH(CH3)CH(CH3)2 1301 CF2CF3 Br HCH(CH3)CH2CH2CH(CH3)2 1302 CF2CF3 Br H CH(CH2CH3)2 1303 CF2CF3 Br HC(CH3)2CH2CH3 1304 CF2CF3 Br H C(CH3)2CH2C(CH3)3 1305 CF2CF3 Br HCH2—CH(OMe)2 1306 CF2CF3 Br H CH2—CH(OEt)2 1307 CF2CF3 Br H CH2CH2—OH1308 CF2CF3 Br H CH2CH2-OMe 1309 CF2CF3 Br Me CH2CH2-OMe 1310 CF2CF3 BrH CH2CH2-OEt 1311 CF2CF3 Br H CH2CH2-SMe 1312 CF2CF3 Br H CH2CH2-CN 1313CF2CF3 Br H CH2CH2-NMe2 1314 CF2CF3 Br H CH2CH2-morpholin-4-yl 1315CF2CF3 Br H CH(CH3)CH2-OMe 1316 CF2CF3 Br H CH(CH3)CH2-NMe2 1317 CF2CF3Br H CH2CH2CH2-OMe 1318 CF2CF3 Br H CH2CH2CH2-SMe 1319 CF2CF3 Br HCH2CH2CH2-OEt 1320 CF2CF3 Br H CH2CH2CH2-OiPr 1321 CF2CF3 Br HCH2CH2CH2-OBu 1322 CF2CF3 Br H CH2—COOCH3 1323 CF2CF3 Br Me CH2—COOCH31324 CF2CF3 Br H CH(CH3)COOMe 1325 CF2CF3 Br H CH(CH3)COOEt 1326 CF2CF3Br H CH2CH2—COOCH3 1327 CF2CF3 Br H CH(COOCH3)2 1328 CF2CF3 Br HCH(COOEt)CH2—CH(CH3)2 1329 CF2CF3 Br H CH(COOMe)CH(CH3)2 1330 CF2CF3 BrH O—CH2CH3 1331 CF2CF3 Br Me O—CH3 1332 CF2CF3 Br H O—CH2CH═CH2 1333CF2CF3 Br H O-tBu 1334 CF2CF3 Br H O-Pr 1335 CF2CF3 Br H O—CH2cPr 1336CF2CF3 Br H O—CH2CH(CH3)2 1337 CF2CF3 Br H O—CH2CF3 1338 CF2CF3 Br HO—CH(CH3)cPr 1339 CF2CF3 Br H O—CH2CH2Cl 1340 CF2CF3 Br H O—CH2C≡CH 1341CF2CF3 Br H O—CH2C≡CCH3 1342 CF2CF3 Br H O—CH(CH3)C≡CH 1343 CF2CF3 Br HCH2-Ph 1344 CF2CF3 Br Me CH2-Ph 1345 CF2CF3 Br H CH2-pyridin-3-yl 1346CF2CF3 Br H CH2-6-Cl-pyridin-3-yl 1347 CF2CF3 Br H CH(CH3)Ph 1348 CF2CF3Br H CH2CH2-Ph 1349 CF2CF3 Br H CH2-2-CF3-Ph 1350 CF2CF3 Br HCH2CH2CHPh2 1351 CF2CF3 Br morpholin-4-yl 1352 CF2CF3 Br piperidin-1-yl1353 CF2CF3 Br thiazolidin-3-yl 1354 CF2CF3 Br pyrrolidin-1-yl 1355CF2CF3 Br 2-methylpyrrolidin-1-yl 1356 CF2CF3 Br ═CH—N(CH3)2 1357 CF2CF3Br ═C(CH3)N(CH3)2 1358 CF2CF3 Br ═CH—N(C2H5)2 1359 CF2CF3 Br═C(CH3)N(C2H5)2 1360 CF2CF3 Br ═CH-piperidine 1361 CF2CF3 Br═CH-morpholine 1362 CF2CF3 Br ═CH-pyrrolidine 1363 CF2CF3 Br Hindan-1-yl 1364 CF2CF3 Br H tetrahydrofuran-2-ylmethyl 1365 CF2CF3 I H H1366 CF3 I H H 1367 CF2CHF2 H H H 1368 CF2CHF2 H H Me 1369 CF2CHF2 H HEt 1370 CF2CHF2 H H Pr 1371 CF2CHF2 H H iPr 1372 CF2CHF2 H H cPr 1373CF2CHF2 H H Bu 1374 CF2CHF2 H H cBu 1375 CF2CHF2 H H tBu 1376 CF2CHF2 HMe Me 1377 CF2CHF2 H Me Et 1378 CF2CHF2 H Me Bu 1379 CF2CHF2 H Me Pr1380 CF2CHF2 H Me iPr 1381 CF2CHF2 H Et Et 1382 CF2CHF2 H Et Pr 1383CF2CHF2 H Et iPr 1384 CF2CHF2 H Pr Pr 1385 CF2CHF2 H H cPentyl 1386CF2CHF2 H H cHexyl 1387 CF2CHF2 H H CH2(CH2)3CH3 1388 CF2CHF2 H HCH2(CH2)4CH3 1389 CF2CHF2 H H CH2-cPr 1390 CF2CHF2 H H CH2-CN 1391CF2CHF2 H H CH2—C(CH3)3 1392 CF2CHF2 H H CH2CF2CF3 1393 CF2CHF2 H HCH2CF3 1394 CF2CHF2 H H CH2(CF2)2CF3 1395 CF2CHF2 H H CH2CH(CH3)CH2CH31396 CF2CHF2 H H CH2C(CH3)2CH2F 1397 CF2CHF2 H H CH2CH(CH3)2 1398CF2CHF2 H H CH2CH(CH2CH3)2 1399 CF2CHF2 H H CH2CH2CH(CH3)2 1400 CF2CHF2H H CH2CH2C(CH3)3 1401 CF2CHF2 H H CH2CH═CH2 1402 CF2CHF2 H Me CH2CH═CH21403 CF2CHF2 H CH2CH═CH2 CH2CH═CH2 1404 CF2CHF2 H H CH2CH═CHCH3 1405CF2CHF2 H H CH2—C(CH3)═CH2 1406 CF2CHF2 H H CH2—C≡CH 1407 CF2CHF2 H MeCH2—C≡CH 1408 CF2CHF2 H H CH(CH3)CH2CH3 1409 CF2CHF2 H H CH(CH3)cPr 1410CF2CHF2 H H CH(CH3)(CH2)2CH3 1411 CF2CHF2 H H CH(CH3)(CH2)4CH3 1412CF2CHF2 H H CH(CH3)(CH2)5CH3 1413 CF2CHF2 H H CH(CH2CH3)(CH2)3CH3 1414CF2CHF2 H H CH(CH3)CH2CH(CH3)2 1415 CF2CHF2 H H CH(CH3)C(CH3)3 1416CF2CHF2 H H CH(CH3)CH(CH3)2 1417 CF2CHF2 H H CH(CH3)CH2CH2CH(CH3)2 1418CF2CHF2 H H CH(CH2CH3)2 1419 CF2CHF2 H H C(CH3)2CH2CH3 1420 CF2CHF2 H HC(CH3)2CH2C(CH3)3 1421 CF2CHF2 H H CH2—CH(OMe)2 1422 CF2CHF2 H HCH2—CH(OEt)2 1423 CF2CHF2 H H CH2CH2—OH 1424 CF2CHF2 H H CH2CH2-OMe 1425CF2CHF2 H Me CH2CH2-OMe 1426 CF2CHF2 H H CH2CH2-OEt 1427 CF2CHF2 H HCH2CH2-SMe 1428 CF2CHF2 H H CH2CH2-CN 1429 CF2CHF2 H H CH2CH2-NMe2 1430CF2CHF2 H H CH2CH2-morpholin-4-yl 1431 CF2CHF2 H H CH(CH3)CH2-OMe 1432CF2CHF2 H H CH(CH3)CH2-NMe2 1433 CF2CHF2 H H CH2CH2CH2-OMe 1434 CF2CHF2H H CH2CH2CH2-SMe 1435 CF2CHF2 H H CH2CH2CH2-OEt 1436 CF2CHF2 H HCH2CH2CH2-OiPr 1437 CF2CHF2 H H CH2CH2CH2-OBu 1438 CF2CHF2 H HCH2—COOCH3 1439 CF2CHF2 H Me CH2—COOCH3 1440 CF2CHF2 H H CH(CH3)COOMe1441 CF2CHF2 H H CH(CH3)COOEt 1442 CF2CHF2 H H CH2CH2—COOCH3 1443CF2CHF2 H H CH(COOCH3)2 1444 CF2CHF2 H H CH(COOEt)CH2—CH(CH3)2 1445CF2CHF2 H H CH(COOMe)CH(CH3)2 1446 CF2CHF2 H H O—CH2CH3 1447 CF2CHF2 H HO—CH3 1448 CF2CHF2 H H O—CH2CH═CH2 1449 CF2CHF2 H H O-tBu 1450 CF2CHF2 HH O-Pr 1451 CF2CHF2 H H O—CH2cPr 1452 CF2CHF2 H H O—CH2CH(CH3)2 1453CF2CHF2 H H O—CH2CF3 1454 CF2CHF2 H H O—CH(CH3)cPr 1455 CF2CHF2 H HO—CH2CH2Cl 1456 CF2CHF2 H H O—CH2C═CH 1457 CF2CHF2 H H O—CH2C≡CCH3 1458CF2CHF2 H H O—CH(CH3)C≡CH 1459 CF2CHF2 H H CH2-Ph 1460 CF2CHF2 H MeCH2-Ph 1461 CF2CHF2 H H CH2-pyridin-3-yl 1462 CF2CHF2 H HCH2-6-Cl-pyridin-3-yl 1463 CF2CHF2 H H CH(CH3)Ph 1464 CF2CHF2 H HCH2CH2-Ph 1465 CF2CHF2 H H CH2-2-CF3-Ph 1466 CF2CHF2 H H CH2CH2CHPh 1467CF2CHF2 H morpholin-4-yl 1468 CF2CHF2 H piperidin-1-yl 1469 CF2CHF2 Hthiazolidin-3-yl 1470 CF2CHF2 H pyrrolidin-1-yl 1471 CF2CHF2 H2-methylpyrrolidin-1-yl 1472 CF2CHF2 H ═CH—N(CH3)2 1473 CF2CHF2 H═C(CH3)N(CH3)2 1474 CF2CHF2 H ═CH—N(C2H5)2 1475 CF2CHF2 H═C(CH3)N(C2H5)2 1476 CF2CHF2 H ═CH-piperidine 1477 CF2CHF2 H═CH-morpholine 1478 CF2CHF2 H ═CH-pyrrolidine 1479 CF2CHF2 H Hindan-1-yl 1480 CF2CHF2 H H tetrahydrofuran-2-ylmethyl 1481 CF2CF2Cl H HH 1482 CF2CF2Cl H H Me 1483 CF2CF2Cl H H Et 1484 CF2CF2Cl H H Pr 1485CF2CF2Cl H H iPr 1486 CF2CF2Cl H H cPr 1487 CF2CF2Cl H H Bu 1488CF2CF2Cl H H cBu 1489 CF2CF2Cl H H tBu 1490 CF2CF2Cl H Me Me 1491CF2CF2Cl H Me Et 1492 CF2CF2Cl H Me Bu 1493 CF2CF2Cl H Me Pr 1494CF2CF2Cl H Me iPr 1495 CF2CF2Cl H Et Et 1496 CF2CF2Cl H Et Pr 1497CF2CF2Cl H Et iPr 1498 CF2CF2Cl H Pr Pr 1499 CF2CF2Cl H H cPentyl 1500CF2CF2Cl H H cHexyl 1501 CF2CF2Cl H H CH2(CH2)3CH3 1502 CF2CF2Cl H HCH2(CH2)4CH3 1503 CF2CF2Cl H H CH2-cPr 1504 CF2CF2Cl H H CH2-CN 1505CF2CF2Cl H H CH2—C(CH3)3 1506 CF2CF2Cl H H CH2CF2CF3 1507 CF2CF2Cl H HCH2CF3 1508 CF2CF2Cl H H CH2(CF2)2CF3 1509 CF2CF2Cl H H CH2CH(CH3)CH2CH31510 CF2CF2Cl H H CH2C(CH3)2CH2F 1511 CF2CF2Cl H H CH2CH(CH3)2 1512CF2CF2Cl H H CH2CH(CH2CH3)2 1513 CF2CF2Cl H H CH2CH2CH(CH3)2 1514CF2CF2Cl H H CH2CH2C(CH3)3 1515 CF2CF2Cl H H CH2CH═CH2 1516 CF2CF2Cl HMe CH2CH═CH2 1517 CF2CF2Cl H CH2CH═CH2 CH2CH═CH2 1518 CF2CF2Cl H HCH2CH═CHCH3 1519 CF2CF2Cl H H CH2—C(CH3)═CH2 1520 CF2CF2Cl H H CH2—C≡CH1521 CF2CF2Cl H Me CH2—C≡CH 1522 CF2CF2Cl H H CH(CH3)CH2CH3 1523CF2CF2Cl H H CH(CH3)cPr 1524 CF2CF2Cl H H CH(CH3)(CH2)2CH3 1525 CF2CF2ClH H CH(CH3)(CH2)4CH3 1526 CF2CF2Cl H H CH(CH3)(CH2)5CH3 1527 CF2CF2Cl HH CH(CH2CH3)(CH2)3CH3 1528 CF2CF2Cl H H CH(CH3)CH2CH(CH3)2 1529 CF2CF2ClH H CH(CH3)C(CH3)3 1530 CF2CF2Cl H H CH(CH3)CH(CH3)2 1531 CF2CF2Cl H HCH(CH3)CH2CH2CH(CH3)2 1532 CF2CF2Cl H H CH(CH2CH3)2 1533 CF2CF2Cl H HC(CH3)2CH2CH3 1534 CF2CF2Cl H H C(CH3)2CH2C(CH3)3 1535 CF2CF2Cl H HCH2—CH(OMe)2 1536 CF2CF2Cl H H CH2—CH(OEt)2 1537 CF2CF2Cl H H CH2CH2—OH1538 CF2CF2Cl H H CH2CH2-OMe 1539 CF2CF2Cl H Me CH2CH2-OMe 1540 CF2CF2ClH H CH2CH2-OEt 1541 CF2CF2Cl H H CH2CH2-SMe 1542 CF2CF2Cl H H CH2CH2-CN1543 CF2CF2Cl H H CH2CH2-NMe2 1544 CF2CF2Cl H H CH2CH2-morpholin-4-yl1545 CF2CF2Cl H H CH(CH3)CH2-OMe 1546 CF2CF2Cl H H CH(CH3)CH2-NMe2 1547CF2CF2Cl H H CH2CH2CH2-OMe 1548 CF2CF2Cl H H CH2CH2CH2-SMe 1549 CF2CF2ClH H CH2CH2CH2-OEt 1550 CF2CF2Cl H H CH2CH2CH2-OiPr 1551 CF2CF2Cl H HCH2CH2CH2-OBu 1552 CF2CF2Cl H H CH2—COOCH3 1553 CF2CF2Cl H Me CH2—COOCH31554 CF2CF2Cl H H CH(CH3)COOMe 1555 CF2CF2Cl H H CH(CH3)COOEt 1556CF2CF2Cl H H CH2CH2—COOCH3 1557 CF2CF2Cl H H CH(COOCH3)2 1558 CF2CF2Cl HH CH(COOEt)CH2—CH(CH3)2 1559 CF2CF2Cl H H CH(COOMe)CH(CH3)2 1560CF2CF2Cl H H O—CH2CH3 1561 CF2CF2Cl H H O—CH3 1562 CF2CF2Cl H HO—CH2CH═CH2 1563 CF2CF2Cl H H O-tBu 1564 CF2CF2Cl H H O-Pr 1565 CF2CF2ClH H O—CH2cPr 1566 CF2CF2Cl H H O—CH2CH(CH3)2 1567 CF2CF2Cl H H O—CH2CF31568 CF2CF2Cl H H O—CH(CH3)cPr 1569 CF2CF2Cl H H O—CH2CH2Cl 1570CF2CF2Cl H H O—CH2C≡CH 1571 CF2CF2Cl H H O—CH2C≡CCH3 1572 CF2CF2Cl H HO—CH(CH3)C≡CH 1573 CF2CF2Cl H H CH2-Ph 1574 CF2CF2Cl H Me CH2-Ph 1575CF2CF2Cl H H CH2-pyridin-3-yl 1576 CF2CF2Cl H H CH2-6-Cl-pyridin-3-yl1577 CF2CF2Cl H H CH(CH3)Ph 1578 CF2CF2Cl H H CH2CH2-Ph 1579 CF2CF2Cl HH CH2-2-CF3-Ph 1580 CF2CF2Cl H H CH2CH2CHPh 1581 CF2CF2Cl Hmorpholin-4-yl 1582 CF2CF2Cl H piperidin-1-yl 1583 CF2CF2Cl Hthiazolidin-3-yl 1584 CF2CF2Cl H pyrrolidin-1-yl 1585 CF2CF2Cl H2-methylpyrrolidin-1-yl 1586 CF2CF2Cl H ═CH—N(CH3)2 1587 CF2CF2Cl H═C(CH3)N(CH3)2 1588 CF2CF2Cl H ═CH—N(C2H5)2 1589 CF2CF2Cl H═C(CH3)N(C2H5)2 1590 CF2CF2Cl H ═CH-piperidine 1591 CF2CF2Cl H═CH-morpholine 1592 CF2CF2Cl H ═CH-pyrrolidine 1593 CF2CF2Cl H Hindan-1-yl 1594 CF2CF2Cl H H tetrahydrofuran-2-ylmethyl 1595 C3F7 H H H1596 C3F7 H H Me 1597 C3F7 H H Et 1598 C3F7 H H Pr 1599 C3F7 H H iPr1600 C3F7 H H cPr 1601 C3F7 H H Bu 1602 C3F7 H H cBu 1603 C3F7 H H tBu1604 C3F7 H Me Me 1605 C3F7 H Me Et 1606 C3F7 H Me Bu 1607 C3F7 H Me Pr1608 C3F7 H Me iPr 1609 C3F7 H Et Et 1610 C3F7 H Et Pr 1611 C3F7 H EtiPr 1612 C3F7 H Pr Pr 1613 C3F7 H H cPentyl 1614 C3F7 H H cHexyl 1615C3F7 H H CH2(CH2)3CH3 1616 C3F7 H H CH2(CH2)4CH3 1617 C3F7 H H CH2-cPr1618 C3F7 H H CH2-CN 1619 C3F7 H H CH2—C(CH3)3 1620 C3F7 H H CH2CF2CF31621 C3F7 H H CH2CF3 1622 C3F7 H H CH2(CF2)2CF3 1623 C3F7 H HCH2CH(CH3)CH2CH3 1624 C3F7 H H CH2C(CH3)2CH2F 1625 C3F7 H H CH2CH(CH3)21626 C3F7 H H CH2CH(CH2CH3)2 1627 C3F7 H H CH2CH2CH(CH3)2 1628 C3F7 H HCH2CH2C(CH3)3 1629 C3F7 H H CH2CH═CH2 1630 C3F7 H Me CH2CH═CH2 1631 C3F7H CH2CH═CH2 CH2CH═CH2 1632 C3F7 H H CH2CH═CHCH3 1633 C3F7 H HCH2—C(CH3)═CH2 1634 C3F7 H H CH2—C≡CH 1635 C3F7 H Me CH2—C≡CH 1636 C3F7H H CH(CH3)CH2CH3 1637 C3F7 H H CH(CH3)cPr 1638 C3F7 H HCH(CH3)(CH2)2CH3 1639 C3F7 H H CH(CH3)(CH2)4CH3 1640 C3F7 H HCH(CH3)(CH2)5CH3 1641 C3F7 H H CH(CH2CH3)(CH2)3CH3 1642 C3F7 H HCH(CH3)CH2CH(CH3)2 1643 C3F7 H H CH(CH3)C(CH3)3 1644 C3F7 H HCH(CH3)CH(CH3)2 1645 C3F7 H H CH(CH3)CH2CH2CH(CH3)2 1646 C3F7 H HCH(CH2CH3)2 1647 C3F7 H H C(CH3)2CH2CH3 1648 C3F7 H H C(CH3)2CH2C(CH3)31649 C3F7 H H CH2—CH(OMe)2 1650 C3F7 H H CH2—CH(OEt)2 1651 C3F7 H HCH2CH2—OH 1652 C3F7 H H CH2CH2-OMe 1653 C3F7 H Me CH2CH2-OMe 1654 C3F7 HH CH2CH2-OEt 1655 C3F7 H H CH2CH2-SMe 1656 C3F7 H H CH2CH2-CN 1657 C3F7H H CH2CH2-NMe2 1658 C3F7 H H CH2CH2-morpholin-4-yl 1659 C3F7 H HCH(CH3)CH2-OMe 1660 C3F7 H H CH(CH3)CH2-NMe2 1661 C3F7 H H CH2CH2CH2-OMe1662 C3F7 H H CH2CH2CH2-SMe 1663 C3F7 H H CH2CH2CH2-OEt 1664 C3F7 H HCH2CH2CH2-OiPr 1665 C3F7 H H CH2CH2CH2-OBu 1666 C3F7 H H CH2—COOCH3 1667C3F7 H Me CH2—COOCH3 1668 C3F7 H H CH(CH3)COOMe 1669 C3F7 H HCH(CH3)COOEt 1670 C3F7 H H CH2CH2—COOCH3 1671 C3F7 H H CH(COOCH3)2 1672C3F7 H H CH(COOEt)CH2—CH(CH3)2 1673 C3F7 H H CH(COOMe)CH(CH3)2 1674 C3F7H H O—CH2CH3 1675 C3F7 H H O—CH3 1676 C3F7 H H O—CH2CH═CH2 1677 C3F7 H HO-tBu 1678 C3F7 H H O-Pr 1679 C3F7 H H O—CH2cPr 1680 C3F7 H HO—CH2CH(CH3)2 1681 C3F7 H H O—CH2CF3 1682 C3F7 H H O—CH(CH3)cPr 1683C3F7 H H O—CH2CH2Cl 1684 C3F7 H H O—CH2C≡CH 1685 C3F7 H H O—CH2C≡CCH31686 C3F7 H H O—CH(CH3)C≡CH 1687 C3F7 H H CH2-Ph 1688 C3F7 H Me CH2-Ph1689 C3F7 H H CH2-pyridin-3-yl 1690 C3F7 H H CH2-6-Cl-pyridin-3-yl 1691C3F7 H H CH(CH3)Ph 1692 C3F7 H H CH2CH2-Ph 1693 C3F7 H H CH2-2-CF3-Ph1694 C3F7 H H CH2CH2CHPh 1695 C3F7 H morpholin-4-yl 1696 C3F7 Hpiperidin-1-yl 1697 C3F7 H thiazolidin-3-yl 1698 C3F7 H pyrrolidin-1-yl1699 C3F7 H 2-methylpyrrolidin-1-yl 1700 C3F7 H ═CH—N(CH3)2 1701 C3F7 H═C(CH3)N(0H3)2 1702 C3F7 H ═CH—N(C2H5)2 1703 C3F7 H ═C(CH3)N(C2H5)2 1704C3F7 H ═CH-piperidine 1705 C3F7 H ═CH-morpholine 1706 C3F7 H═CH-pyrrolidine 1707 C3F7 H H indan-1-yl 1708 C3F7 H Htetrahydrofuran-2-ylmethyl 1709 CF(CF3)2 H H H 1710 C3F7 Cl H H 1711C3F7 Cl H Me 1712 C3F7 Cl H Et 1713 C3F7 Cl H Pr 1714 C3F7 Cl H iPr 1715C3F7 Cl H cPr 1716 C3F7 Cl H Bu 1717 C3F7 Cl H cBu 1718 C3F7 Cl H tBu1719 C3F7 Cl Me Me 1720 C3F7 Cl Et Et 1721 C3F7 Cl H CH2-cPr 1722 C3F7Cl H CH2—C(CH3)3 1723 C3F7 Cl H CH2CH(CH3)2 1724 C3F7 Cl HCH2CH(CH2CH3)2 1725 C3F7 Cl H CH2CH2CH(CH3)2 1726 C3F7 Cl HCH2CH2C(CH3)3 1727 C3F7 Cl H CH2CH═CH2 1728 C3F7 Cl H CH2—C(CH3)═CH21729 C3F7 Cl H CH2—CCH 1730 C3F7 Cl Me CH2—CCH 1731 C3F7 Cl HCH(CH3)CH2CH3 1732 C3F7 Cl H CH(CH3)cPr 1733 C3F7 Cl H CH(CH3)(CH2)2CH31734 C3F7 Cl H CH(CH3)(CH2)4CH3 1735 C3F7 Cl H CH(CH3)CH2CH(CH3)2 1736C3F7 Cl H CH(CH3)C(CH3)3 1737 C3F7 Cl H CH(CH3)CH(CH3)2 1738 C3F7 Cl HCH(CH2CH3)2 1739 C3F7 Cl H CH2—CH(OMe)2 1740 C3F7 Cl H CH2—CH(OEt)2 1741C3F7 Cl H CH2CH2—OH 1742 C3F7 Cl H CH2CH2-OMe 1743 C3F7 Cl Me CH2CH2-OMe1744 C3F7 Cl H CH(CH3)CH2-OMe 1745 C3F7 Cl H CH2CH2CH2-OMe 1746 C3F7 ClH CH2—COOCH3 1747 C3F7 Cl Me CH2—COOCH3 1748 C3F7 Cl H CH(CH3)COOMe 1749C3F7 Cl H CH(CH3)COOEt 1750 C3F7 Cl H CH2CH2—COOCH3 1751 C3F7 Br H H1752 C3F7 Br H Me 1753 C3F7 Br H Et 1754 C3F7 Br H Pr 1755 C3F7 Br H iPr1756 C3F7 Br H cPr 1757 C3F7 Br H Bu 1758 C3F7 Br H cBu 1759 C3F7 Br HtBu 1760 C3F7 Br Me Me 1761 C3F7 Br Et Et 1762 C3F7 Br H CH2-cPr 1763C3F7 Br H CH2—C(CH3)3 1764 C3F7 Br H CH2CH(CH3)2 1765 C3F7 Br HCH2CH(CH2CH3)2 1766 C3F7 Br H CH2CH2CH(CH3)2 1767 C3F7 Br HCH2CH2C(CH3)3 1768 C3F7 Br H CH2CH═CH2 1769 C3F7 Br H CH2—C(CH3)═CH21770 C3F7 Br H CH2—CCH 1771 C3F7 Br Me CH2—CCH 1772 C3F7 Br HCH(CH3)CH2CH3 1773 C3F7 Br H CH(CH3)cPr 1774 C3F7 Br H CH(CH3)(CH2)2CH31775 C3F7 Br H CH(CH3)(CH2)4CH3 1776 C3F7 Br H CH(CH3)CH2CH(CH3)2 1777C3F7 Br H CH(CH3)C(CH3)3 1778 C3F7 Br H CH(CH3)CH(CH3)2 1779 C3F7 Br HCH(CH3)CH2CH2CH(CH3)2 1780 C3F7 Br H CH(CH2CH3)2 1781 C3F7 Br HCH2—CH(OMe)2 1782 C3F7 Br H CH2—CH(OEt)2 1783 C3F7 Br H CH2CH2—OH 1784C3F7 Br H CH2CH2-OMe 1785 C3F7 Br H CH(CH3)CH2-OMe 1786 C3F7 Br HCH2CH2CH2-OMe 1787 C3F7 Br H CH2—COOCH3 1788 C3F7 Br Me CH2—COOCH3 1789C3F7 Br H CH(CH3)COOMe 1790 C3F7 Br H CH(CH3)COOEt 1791 C3F7 Br HCH2CH2—COOCH3 1792 C3F7 I H H 1793 C3F7 I H Me 1794 C3F7 I H Et 1795C3F7 I H Pr 1796 C3F7 I H iPr 1797 C3F7 I H cPr 1798 C3F7 I H Bu 1799C3F7 I H cBu 1800 C3F7 I H tBu 1801 C3F7 I Me Me 1802 C3F7 I Et Et 1803C3F7 I H CH2-cPr 1804 C3F7 I H CH2—C(CH3)3 1805 C3F7 I H CH2CH(CH3)21806 C3F7 I H CH2CH(CH2CH3)2 1807 C3F7 I H CH2CH2CH(CH3)2 1808 C3F7 I HCH2CH2C(CH3)3 1809 C3F7 I H CH2CH═CH2 1810 C3F7 I H CH2—C(CH3)═CH2 1811C3F7 I H CH2—CCH 1812 C3F7 I Me CH2—CCH 1813 C3F7 I H CH(CH3)CH2CH3 1814C3F7 I H CH(CH3)cPr 1815 C3F7 I H CH(CH3)(CH2)2CH3 1816 C3F7 I HCH(CH3)(CH2)4CH3 1817 C3F7 I H CH(CH3)CH2CH(CH3)2 1818 C3F7 I HCH(CH3)C(CH3)3 1819 C3F7 I H CH(CH3)CH(CH3)2 1820 C3F7 I H CH(CH2CH3)21821 C3F7 I H CH2—CH(OMe)2 1822 C3F7 I H CH2—CH(OEt)2 1823 C3F7 I HCH2CH2—OH 1824 C3F7 I H CH2CH2-OMe 1825 C3F7 I Me CH2CH2-OMe 1826 C3F7 IH CH(CH3)CH2-OMe 1827 C3F7 I H CH2CH2CH2-OMe 1828 C3F7 I H CH2—COOCH31829 C3F7 I Me CH2—COOCH3 1830 C3F7 I H CH(CH3)COOMe 1831 C3F7 I HCH(CH3)COOEt 1832 C3F7 I H CH2CH2—COOCH3 1833 CF3 I H Me 1834 CF3 I H Et1835 CF3 I H Pr 1836 CF3 I H iPr 1837 CF3 I H cPr 1838 CF3 I H Bu 1839CF3 I H cBu 1840 CF3 I H tBu 1841 CF3 I Me Me 1842 CF3 I Et Et 1843 CF3I H CH2(CH2)3CH3 1844 CF3 I H CH2(CH2)4CH3 1845 CF3 I H CH2-cPr 1846 CF3I H CH2—C(CH3)3 1847 CF3 I H CH2CH(CH3)2 1848 CF3 I H CH2CH(CH2CH3)21849 CF3 I H CH2CH2CH(CH3)2 1850 CF3 I H CH2CH2C(CH3)3 1851 CF3 I HCH2CH═CH2 1852 CF3 I H CH2—C(CH3)═CH2 1853 CF3 I H CH2—CCH 1854 CF3 I HCH(CH3)CH2CH3 1855 CF3 I H CH(CH3)cPr 1856 CF3 I H CH(CH3)(CH2)2CH3 1857CF3 I H CH(CH3)(CH2)4CH3 1858 CF3 I H CH(CH3)CH2CH(CH3)2 1859 CF3 I HCH(CH3)C(CH3)3 1860 CF3 I H CH(CH3)CH(CH3)2 1861 CF3 I H CH(CH2CH3)21862 CF3 I H C(CH3)2CH2CH3 1863 CF3 I H C(CH3)2CH2C(CH3)3 1864 CF3 I HCH2—CH(OMe)2 1865 CF3 I H CH2—CH(OEt)2 1866 CF3 I H CH2CH2—OH 1867 CF3 IH CH2CH2-OMe 1868 CF3 I Me CH2CH2-OMe 1869 CF3 I H CH(CH3)CH2-OMe 1870CF3 I H CH2CH2CH2-OMe 1871 CF3 I H CH2—COOCH3 1872 CF3 I Me CH2—COOCH31873 CF3 I H CH(CH3)COOMe 1874 CF3 I H CH(CH3)COOEt 1875 CF3 I HCH2CH2—COOCH3 1876 CF2Cl I H H 1877 CF2Cl I H Me 1878 CF2Cl I H Et 1879CF2Cl I H Pr 1880 CF2Cl I H iPr 1881 CF2Cl I H cPr 1882 CF2Cl I H Bu1883 CF2Cl I H cBu 1884 CF2Cl I H tBu 1885 CF2Cl I Me Me 1886 CF2Cl I HCH2-cPr 1887 CF2Cl I H CH2—C(CH3)3 1888 CF2Cl I H CH2CH(CH3)2 1889 CF2ClI H CH2CH(CH2CH3)2 1890 CF2Cl I H CH2CH2CH(CH3)2 1891 CF2Cl I HCH2CH2C(CH3)3 1892 CF2Cl I H CH2CH═CH2 1893 CF2Cl I Me CH2CH═CH2 1894CF2Cl I H CH2—C(CH3)═CH2 1895 CF2Cl I H CH2—CCH 1896 CF2Cl I Me CH2—CCH1897 CF2Cl I H CH(CH3)CH2CH3 1898 CF2Cl I H CH(CH3)cPr 1899 CF2Cl I HCH(CH3)(CH2)2CH3 1900 CF2Cl I H CH(CH3)(CH2)4CH3 1901 CF2Cl I HCH(CH3)(CH2)5CH3 1902 CF2Cl I H CH(CH2CH3)(CH2)3CH3 1903 CF2Cl I HCH(CH3)CH2CH(CH3)2 1904 CF2Cl I H CH(CH3)C(CH3)3 1905 CF2Cl I HCH(CH3)CH(CH3)2 1906 CF2Cl I H CH(CH3)CH2CH2CH(CH3)2 1907 CF2Cl I HCH(CH2CH3)2 1908 CF2Cl I H C(CH3)2CH2CH3 1909 CF2Cl I HC(CH3)2CH2C(CH3)3 1910 CF2Cl I H CH2—CH(OMe)2 1911 CF2Cl I HCH2—CH(OEt)2 1912 CF2Cl I H CH2CH2—OH 1913 CF2Cl I H CH2CH2-OMe 1914CF2Cl I Me CH2CH2-OMe 1915 CF2Cl I H CH2CH2-OEt 1916 CF2Cl I HCH(CH3)CH2-OMe 1917 CF2Cl I H CH2CH2CH2-OMe 1918 CF2Cl I H CH2—COOCH31919 CF2Cl I Me CH2—COOCH3 1920 CF2Cl I H CH(CH3)COOMe 1921 CF2Cl I HCH(CH3)COOEt 1922 CF2Cl I H CH2CH2—COOCH3 1923 CF2CF3 I H Me 1924 CF2CF3I H Et 1925 CF2CF3 I H Pr 1926 CF2CF3 I H iPr 1927 CF2CF3 I H cPr 1928CF2CF3 I H Bu 1929 CF2CF3 I H cBu 1930 CF2CF3 I H tBu 1931 CF2CF3 I MeMe 1932 CF2CF3 I Et Et 1933 CF2CF3 I H CH2-cPr 1934 CF2CF3 I HCH2—C(CH3)3 1935 CF2CF3 I H CH2CH(CH3)2 1936 CF2CF3 I H CH2CH(CH2CH3)21937 CF2CF3 I H CH2CH2CH(CH3)2 1938 CF2CF3 I H CH2CH2C(CH3)3 1939 CF2CF3I H CH2CH═CH2 1940 CF2CF3 I Me CH2CH═CH2 1941 CF2CF3 I H CH2—C(CH3)═CH21942 CF2CF3 I H CH2—CCH 1943 CF2CF3 I Me CH2—CCH 1944 CF2CF3 I HCH(CH3)CH2CH3 1945 CF2CF3 I H CH(CH3)cPr 1946 CF2CF3 I HCH(CH3)(CH2)2CH3 1947 CF2CF3 I H CH(CH3)(CH2)4CH3 1948 CF2CF3 I HCH(CH3)CH2CH(CH3)2 1949 CF2CF3 I H CH(CH3)C(CH3)3 1950 CF2CF3 I HCH(CH3)CH(CH3)2 1951 CF2CF3 I H CH(CH2CH3)2 1952 CF2CF3 I H CH2—CH(OMe)21953 CF2CF3 I H CH2—CH(OEt)2 1954 CF2CF3 I H CH2CH2—OH 1955 CF2CF3 I HCH2CH2-OMe 1956 CF2CF3 I Me CH2CH2-OMe 1957 CF2CF3 I H CH(CH3)CH2-OMe1958 CF2CF3 I H CH2CH2CH2-OMe 1959 CF2CF3 I H CH2—COOCH3 1960 CF2CF3 IMe CH2—COOCH3 1961 CF2CF3 I H CH(CH3)COOMe 1962 CF2CF3 I H CH(CH3)COOEt1963 CF2CF3 I H CH2CH2—COOCH3 1964 CF2CF2Cl Cl H H 1965 CF2CF2Cl Cl H Me1966 CF2CF2Cl Cl H Et 1967 CF2CF2Cl Cl H Pr 1968 CF2CF2Cl Cl H iPr 1969CF2CF2Cl Cl H cPr 1970 CF2CF2Cl Cl H Bu 1971 CF2CF2Cl Cl H cBu 1972CF2CF2Cl Cl H tBu 1973 CF2CF2Cl Cl Me Me 1974 CF2CF2Cl Cl Et Et 1975CF2CF2Cl Cl H CH2-cPr 1976 CF2CF2Cl Cl H CH2—C(CH3)3 1977 CF2CF2Cl Cl HCH2CH(CH3)2 1978 CF2CF2Cl Cl H CH2CH(CH2CH3)2 1979 CF2CF2Cl Cl HCH2CH2CH(CH3)2 1980 CF2CF2Cl Cl H CH2CH2C(CH3)3 1981 CF2CF2Cl Cl HCH2CH═CH2 1982 CF2CF2Cl Cl Me CH2CH═CH2 1983 CF2CF2Cl Cl HCH2—C(CH3)═CH2 1984 CF2CF2Cl Cl H CH2—CCH 1985 CF2CF2Cl Cl Me CH2—CCH1986 CF2CF2Cl Cl H CH(CH3)CH2CH3 1987 CF2CF2Cl Cl H CH(CH3)cPr 1988CF2CF2Cl Cl H CH(CH3)(CH2)2CH3 1989 CF2CF2Cl Cl H CH(CH3)(CH2)4CH3 1990CF2CF2Cl Cl H CH(CH3)CH2CH(CH3)2 1991 CF2CF2Cl Cl H CH(CH3)C(CH3)3 1992CF2CF2Cl Cl H CH(CH3)CH(CH3)2 1993 CF2CF2Cl Cl H CH(CH2CH3)2 1994CF2CF2Cl Cl H CH2—CH(OMe)2 1995 CF2CF2Cl Cl H CH2—CH(OEt)2 1996 CF2CF2ClCl H CH2CH2—OH 1997 CF2CF2Cl Cl H CH2CH2-OMe 1998 CF2CF2Cl Cl MeCH2CH2-OMe 1999 CF2CF2Cl Cl H CH(CH3)CH2-OMe 2000 CF2CF2Cl Cl HCH2CH2CH2-OMe 2001 CF2CF2Cl Cl H CH2—COOCH3 2002 CF2CF2Cl Cl MeCH2—COOCH3 2003 CF2CF2Cl Cl H CH(CH3)COOMe 2004 CF2CF2Cl Cl HCH(CH3)COOEt 2005 CF2CF2Cl Cl H CH2CH2—COOCH3 2006 CF2CF2Cl Br H H 2007CF2CF2Cl Br H Me 2008 CF2CF2Cl Br H Et 2009 CF2CF2Cl Br H Pr 2010CF2CF2Cl Br H iPr 2011 CF2CF2Cl Br H cPr 2012 CF2CF2Cl Br H Bu 2013CF2CF2Cl Br H cBu 2014 CF2CF2Cl Br H tBu 2015 CF2CF2Cl Br Me Me 2016CF2CF2Cl Br Et Et 2017 CF2CF2Cl Br H CH2-cPr 2018 CF2CF2Cl Br HCH2—C(CH3)3 2019 CF2CF2Cl Br H CH2CH(CH3)2 2020 CF2CF2Cl Br HCH2CH(CH2CH3)2 2021 CF2CF2Cl Br H CH2CH2CH(CH3)2 2022 CF2CF2Cl Br HCH2CH2C(CH3)3 2023 CF2CF2Cl Br H CH2CH═CH2 2024 CF2CF2Cl Br Me CH2CHCH22025 CF2CF2Cl Br H CH2—C(CH3)═CH2 2026 CF2CF2Cl Br H CH2—CCH 2027CF2CF2Cl Br Me CH2—CCH 2028 CF2CF2Cl Br H CH(CH3)CH2CH3 2029 CF2CF2Cl BrH CH(CH3)cPr 2030 CF2CF2Cl Br H CH(CH3)(CH2)2CH3 2031 CF2CF2Cl Br HCH(CH3)(CH2)4CH3 2032 CF2CF2Cl Br H CH(CH3)CH2CH(CH3)2 2033 CF2CF2Cl BrH CH(CH3)C(CH3)3 2034 CF2CF2Cl Br H CH(CH3)CH(CH3)2 2035 CF2CF2Cl Br HCH(CH2CH3)2 2036 CF2CF2Cl Br H CH2—CH(OMe)2 2037 CF2CF2Cl Br HCH2—CH(OEt)2 2038 CF2CF2Cl Br H CH2CH2—OH 2039 CF2CF2Cl Br H CH2CH2-OMe2040 CF2CF2Cl Br Me CH2CH2-OMe 2041 CF2CF2Cl Br H CH(CH3)CH2-OMe 2042CF2CF2Cl Br H CH2CH2CH2-OMe 2043 CF2CF2Cl Br H CH2—COOCH3 2044 CF2CF2ClBr Me CH2—COOCH3 2045 CF2CF2Cl Br H CH(CH3)COOMe 2046 CF2CF2Cl Br HCH(CH3)COOEt 2047 CF2CF2Cl Br H CH2CH2—COOCH3 2048 CF2CF2Cl I H H 2049CF2CF2Cl I H Me 2050 CF2CF2Cl I H Et 2051 CF2CF2Cl I H Pr 2052 CF2CF2ClI H iPr 2053 CF2CF2Cl I H cPr 2054 CF2CF2Cl I H Bu 2055 CF2CF2Cl I H cBu2056 CF2CF2Cl I H tBu 2057 CF2CF2Cl I Me Me 2058 CF2CF2Cl I Et Et 2059CF2CF2Cl I H CH2-cPr 2060 CF2CF2Cl I H CH2—C(CH3)3 2061 CF2CF2Cl I HCH2CH(CH3)2 2062 CF2CF2Cl I H CH2CH(CH2CH3)2 2063 CF2CF2Cl I HCH2CH2CH(CH3)2 2064 CF2CF2Cl I H CH2CH2C(CH3)3 2065 CF2CF2Cl I HCH2CH═CH2 2066 CF2CF2Cl I Me CH2CH═CH2 2067 CF2CF2Cl I H CH2—C(CH3)═CH22068 CF2CF2Cl I H CH2—CCH 2069 CF2CF2Cl I Me CH2—CCH 2070 CF2CF2Cl I HCH(CH3)CH2CH3 2071 CF2CF2Cl I H CH(CH3)cPr 2072 CF2CF2Cl I HCH(CH3)(CH2)2CH3 2073 CF2CF2Cl I H CH(CH3)(CH2)4CH3 2074 CF2CF2Cl I HCH(CH3)CH2CH(CH3)2 2075 CF2CF2Cl I H CH(CH3)C(CH3)3 2076 CF2CF2Cl I HCH(CH3)CH(CH3)2 2077 CF2CF2Cl I H CH(CH2CH3)2 2078 CF2CF2Cl I HCH2—CH(OMe)2 2079 CF2CF2Cl I H CH2—CH(OEt)2 2080 CF2CF2Cl I H CH2CH2—OH2081 CF2CF2Cl I H CH2CH2-OMe 2082 CF2CF2Cl I Me CH2CH2-OMe 2083 CF2CF2ClI H CH(CH3)CH2-OMe 2084 CF2CF2Cl I H CH2CH2CH2-OMe 2085 CF2CF2Cl I HCH2—COOCH3 2086 CF2CF2Cl I Me CH2—COOCH3 2087 CF2CF2Cl I H CH(CH3)COOMe2088 CF2CF2Cl I H CH(CH3)COOEt 2089 CF2CF2Cl I H CH2CH2—COOCH3 2090CFClCF3 H H H 2091 CFClCF3 H H Me 2092 CFClCF3 H H Et 2093 CFClCF3 H HPr 2094 CFClCF3 H H iPr 2095 CFClCF3 H H cPr 2096 CFClCF3 H H Bu 2097CFClCF3 H H cBu 2098 CFClCF3 H H tBu 2099 CFClCF3 H Me Me 2100 CFClCF3 HEt Et 2101 CFClCF3 H H CH2-cPr 2102 CFClCF3 H H CH2—C(CH3)3 2103 CFClCF3H H CH2CH(CH3)2 2104 CFClCF3 H H CH2CH(CH2CH3)2 2105 CFClCF3 H HCH2CH2CH(CH3)2 2106 CFClCF3 H H CH2CH2C(CH3)3 2107 CFClCF3 H H CH2CH═CH22108 CFClCF3 H Me CH2CH═CH2 2109 CFClCF3 H H CH2—C(CH3)═CH2 2110 CFClCF3H H CH2—CCH 2111 CFClCF3 H Me CH2—CCH 2112 CFClCF3 H H CH(CH3)CH2CH32113 CFClCF3 H H CH(CH3)cPr 2114 CFClCF3 H H CH(CH3)(CH2)2CH3 2115CFClCF3 H H CH(CH3)(CH2)4CH3 2116 CFClCF3 H H CH(CH3)CH2CH(CH3)2 2117CFClCF3 H H CH(CH3)C(CH3)3 2118 CFClCF3 H H CH(CH3)CH(CH3)2 2119 CFClCF3H H CH(CH2CH3)2 2120 CFClCF3 H H CH2—CH(OMe)2 2121 CFClCF3 H HCH2—CH(OEt)2 2122 CFClCF3 H H CH2CH2—OH 2123 CFClCF3 H H CH2CH2-OMe 2124CFClCF3 H Me CH2CH2-OMe 2125 CFClCF3 H H CH(CH3)CH2-OMe 2126 CFClCF3 H HCH2CH2CH2-OMe 2127 CFClCF3 H H CH2—COOCH3 2128 CFClCF3 H Me CH2—COOCH32129 CFClCF3 H H CH(CH3)COOMe 2130 CFClCF3 H H CH(CH3)COOEt 2131 CFClCF3H H CH2CH2—COOCH3 2132 CFClCF3 Br H H 2133 CFClCF3 Br H Me 2134 CFClCF3Br H Et 2135 CFClCF3 Br H Pr 2136 CFClCF3 Br H iPr 2137 CFClCF3 Br H cPr2138 CFClCF3 Br H Bu 2139 CFClCF3 Br H cBu 2140 CFClCF3 Br H tBu 2141CFClCF3 Br Me Me 2142 CFClCF3 Br Et Et 2143 CFClCF3 Br H CH2-cPr 2144CFClCF3 Br H CH2—C(CH3)3 2145 CFClCF3 Br H CH2CH(CH3)2 2146 CFClCF3 Br HCH2CH(CH2CH3)2 2147 CFClCF3 Br H CH2CH2CH(CH3)2 2148 CFClCF3 Br HCH2CH2C(CH3)3 2149 CFClCF3 Br H CH2CH═CH2 2150 CFClCF3 Br Me CH2CH═CH22151 CFClCF3 Br H CH2—C(CH3)═CH2 2152 CFClCF3 Br H CH2—C≡CH 2153 CFClCF3Br Me CH2—C≡CH 2154 CFClCF3 Br H CH(CH3)CH2CH3 2155 CFClCF3 Br HCH(CH3)cPr 2156 CFClCF3 Br H CH(CH3)(CH2)2CH3 2157 CFClCF3 Br HCH(CH3)(CH2)4CH3 2158 CFClCF3 Br H CH(CH3)CH2CH(CH3)2 2159 CFClCF3 Br HCH(CH3)C(CH3)3 2160 CFClCF3 Br H CH(CH3)CH(CH3)2 2161 CFClCF3 Br HCH(CH2CH3)2 2162 CFClCF3 Br H CH2—CH(OMe)2 2163 CFClCF3 Br HCH2—CH(OEt)2 2164 CFClCF3 Br H CH2CH2—OH 2165 CFClCF3 Br H CH2CH2-OMe2166 CFClCF3 Br Me CH2CH2-OMe 2167 CFClCF3 Br H CH(CH3)CH2-OMe 2168CFClCF3 Br H CH2CH2CH2-OMe 2169 CFClCF3 Br H CH2—COOCH3 2170 CFClCF3 BrMe CH2—COOCH3 2171 CFClCF3 Br H CH(CH3)COOMe 2172 CFClCF3 Br HCH(CH3)COOEt 2173 CFClCF3 Br H CH2CH2—COOCH3

TABLE 2 NMR data of compounds from Table 1 Ex. No. 1H-NMR data 1 [CDCl3]3.03 (d, 3H); 6.88 (d, 1H); 8.65 (d, 1H); 9.22 (br, 1H) 2 [CDCl3] 1.25(t, 3H); 3.5 (m, 2H); 6.92 (d, 1H); 8.72 (d, 1H), 9.33 (br, 1H), 13.4(br, 1H) 3 [CDCl3] 1.02 (t, 3H); 1.62 (m, 2H); 3.42 (m, 2H); 6.90 (d,1H); 8.70 (d, 1H); 9.35 (br, 1H); 13.3 (br, 1H) 4 [CDCl3] 1.25 (d, 6H);4.22 (m, 1H); 6.90 (d, 1H); 8.68 (d, 1H); 9.22 (d, br, 1H) 5 [CDCl3]0.61 (m, 2H); 0.89 (m, 2H); 3.00 (m, 1H); 6.90 (d, 1H); 8.68 (d, 1H),9.31 (br, 1H) 6 [CDCl3] 0.96 (t, 3H); 1.41 (m, 2H); 1.61 (m, 2H); 3.48(q, 2H); 6.90 (d, 1H); 8.70 (d, 1H); 9.31 (br, 1H); 13.3 (br, 1H) 7[CDCl3] 1.80 (m, 2H); 2.00 (m, 2H); 2.42 (m, 2H); 4.55 (m, 1H); 6.88 (d,1H); 8.65 (d, 1H); 9.50 (br, 1H) 8 [CDCl3] 1.44 (s, 9H); 6.90 (d, 1H);8.62 (d, 1H); 9.32 (br, 1H); 13.4 (br, 1H) 9 [CDCl3] 3.05 (s, 6H); 7.10(d, 1H); 7.77 (d, 1H) 10 [CDCl3] 1.22 (t, 3H); 3.02 (s, 3H); 3.46 (m,2H); 7.08 (d, 1H); 7.77 (d, 1H) 11 [CDCl3] 0.90 (t, 3H); 1.30 (br, 2H);1.60 (m, 2H); 3.03 (s, 3H); 3.42 (br, 2H); 7.10 (d, 1H); 7.74 (d, 1H) 13[CDCl3] 1.20 (d, 6H); 2.90 (s, 3H); 4.05 (m, br, 1H); 7.03 (d, 1H); 8.68(d, 1H); 11.2 (br) 14 [CDCl3] 1.20 (t, 6H); 3.40 (m, 4H); 7.05 (d, 1H);8.70 (d, 1H); 11.1 (br) 16 [CDCl3] 1.21 (m, 9H); 3.39 (q, 2H); 4.0 (br,1H); 7.04 (d, 1H); 7.68 (d, 1H); 10.6 (br, 1H) 18 [CDCl3] 1.5-1.8 (m,8H); 4.40 (m, 1H); 6.90 (d, 1H); 8.68 (d, 1H); 9.40 (d, br, 1H); 13.5(br) 19 [CDCl3] 1.2-1.5 (m, 6H); 1.76 (m, 2H); 2.00 (m, 2H); 4.00 (m,1H); 6.90 (d, 1H); 8.68 (d, 1H); 9.30 (d, br, 1H); 13.4 (br, 1H) 20[CDCl3] 0.90 (t, 3H); 1.38 (m, 4H); 1.61 (m, 2H); 3.41 (m, 2H); 6.86 (d,1H); 8.63 (d, 1H); 9.20 (t, 1H) 22 [CDCl3] 0.30 (m, 2H); 0.60 (m, 2H);1.05 (m, 1H); 3.30 (m, 2H); 6.90 (d, 1H), 8.70 (d, 1H); 9.38 (br, 1H) 24[CDCl3] 1.00 (s, 9H); 3.28 (d, 2H); 6.90 (d, 1H); 8.73 (d, 1H); 9.4 (br,1H); 13.2 (br, 1H) 25 [CDCl3] 4.18 (dt, 2H); 6.92 (d, 1H); 8.72 (d, 1H);9.8 (t, br, 1H) 26 [CDCl3] 4.11 (m, 2H); 6.90 (d, 1H); 8.70 (d, 1H);9.80 (br, 1H); 12.16 (br, 1H) 27 [CDCl3] 4.22 (dt; 2H); 6.93 (d, 1H);8.72 (d, 1H); 9.80 (t, br, 1H) 30 [CDCl3] 1.00 (d, 6H); 1.87 (m, 1H);3.29 (t, 2H); 6.88 (d, 1H); 8.64 (d, 1H); 9.32 (br, 1H); 12.5 (br, 1H)32 [CDCl3] 0.95 (d, 6H); 1.48 (m, 2H); 1.70 (m, 1H); 3.48 (m, 2H); 6.88(d, 1H); 8.65 (d, 1H); 9.22 (br, 1H), 12.6 (br) 34 [CDCl3] 4.10 (t, 2H);5.22 (dd, 2H); 5.95 (m, 1H); 6.90 (d, 1H); 8.70 (d, 1H); 9.40 (br, 1H);12.7 (br, 1H) 36 [CDCl3] 4.0 (m, 4H); 5.21 (d, 4H); 5.80 (m, 2H); 7.04(d, 1H); 7.78 (d, 1H); 11.0 (br) 38 [CDCl3] 1.80 (s, 3H); 4.02 (d, 2H);4.93 (d, 2H); 6.89 (d 1H); 8.70 (d, 1H); 9.43 (br, 1H); 13.2 (br, 1H) 39[CDCl3] 2.24 (t, 1H); 4.22 (m, 2H); 6.88 (d, 1H); 8.68 (d, 1H); 9.50(br, 1H) 40 [CDCl3] 2.30 (s, 1H); 3.12 (s, 3H); 4.22 (br, 2H); 7.04 (d,1H); 7.84 (d, 1H); 10.9 (br) 41 [CDCl3] 0.95 (t, 3H); 1.22 (d, 3H); 1.58(m, 2H); 4.10 (m, 1H); 6.88 (d, 1H); 8.66 (d, 1H); 9.20 (br, 1H); 13.0(br, 1H) 43 [DMSO] 0.93 (t, 3H); 1.16 (d, 3H); 1.30 (m, 2H); 1.48 (m,2H); 4.00 (m, 1H); 7.35 (br, 1H); 7.39 (d, 1H); 8.40 (d, 1H); 13.40 (br)44 [DMSO] 0.87 (t, 3H); 1.15 (d, 3H); 1.27 (m, 6H); 1.48 (m, 2H); 4.00(m, 1H); 7.33 (d, 1H); 8.40 (d, 1H); 8.80 (br, 1H), 13.4 (br, 1H) 47[CDCl3] 0.93 (d, 6H); 1.22 (d, 3H); 1.35 (m, 1H), 1.50 (m, 1H); 1.65 (m,1H); 4.23 (m, 1H); 6.90 (d, 1H); 8.64 (d, 1H); 9.20 (d, br, 1H); 13.3(br, 1H) 48 [CDCl3] 0.96 (s, 9H); 1.18 (d, 3H); 4.10 (m, 1H); 6.90 (d,1H); 8.74 (d, 1H); 9.37 (d, br, 1H), 13.6 (br, 1H) 49 [CDCl3] 0.95 (dt,6H); 1.20 (d, 3H); 1.80 (m, 1H); 4.07 (m, 1H); 6.90 (d, 1H); 8.70 (d,1H); 9.30 (d, br, 1H); 13.6 (br) 51 [DMSO] 0.85 (t, 6H); 1.45 (m, 2H);1.55 (m, 2H); 3.80 (m, 1H); 7.33 (d, br, 1H); 8.38 (d, 1H); 8.65 (br,1H); 13.5 (br, 1H) 54 [CDCl3] 3.40 (s, 6H); 3.62 (t, 2H); 4.50 (t, 1H);6.89 (d, 1H); 8.65 (d, 1H); 9.30 (br, 1H); 12.4 (br, 1H) 55 [CDCl3] 1.21(t, 6H); 3.60 (m, 4H); 3.72 (m, 2H); 4.61 (t, 1H); 6.88 (d, 1H); 8.61(d, 1H); 9.28 (br, 1H), 12.0 (br) 56 [DMSO] 3.40 (m, 2H); 3.53 (m, 2H);7.32 (d, br, 1H); 8.45 (d, 1H); 9.05 (br, 1H); 13.6 (br, 1H) 57 [CDCl3]3.40 (s, 3H); 3.56 (t, 2H); 3.64 (m, 2H); 6.90 (d, 1H), 8.65 (d, 1H);9.35 (br, 1H) 64 [CDCl3] 1.25 (d, 3H); 3.40 (s, 3H); 3.43 (d, 2H); 4.37(m, 1H); 6.89 (d, 1H); 8.64 (d, 1H); 9.30 (d, br, 1H); 13.0 (br, 1H) 66[CDCl3] 1.90 (m, 2H); 3.34 (s, 3H); 3.46 (t, 2H); 3.55 (q, 2H); 6.90 (d,1H); 8.60 (d, 1H); 9.23 (br, 1H); 12.5 (br) 71 [CDCl3] 3.80 (s, 3H);4.22 (d, 2H); 6.88 (d, 1H); 8.64 (d, 1H); 9.62 (t, 1H), 72 [CDCl3] 3.10(s, 3H); 3.75 (s, 3H); 4.25 (s, 2H); 7.18 (d, 1H); 7.80 (d, 1H) 75[CDCl3] 2.64 (t, 2H); 3.69 (s, 3H); 3.73 (m, 2H); 6.88 (d, 1H); 8.61 (d,1H); 9.41 (t, br, 1H); 12.2 (br, 1H) 76 [CDCl3] 3.83 (s, 6H); 5.42 (d,1H); 6.90 (d, 1H); 8.63 (d, 1H), 10.2 (br, 1H), 77 [CDCl3] 0.99 (t, 6H);1.25 (t, 3H)1.75 (m, 3H); 4.20 (m, 2H); 4.72 (m, 1H); 6.90 (d, 1H); 8.64(d, 1H); 9.60 (d, br, 1H) 78 [CDCl3] 1.05 (t, 6H); 2.30 (m, 1H); 3.78(s, 3H); 4.72 (m, 1H); 6.90 (d, 1H); 8.70 (d, 1H); 9.76 (d, br, 1H),13.6 (br, 1H) 79 [CDCl3] 1.35 (t, 3H); 4.10 (q, 2H); 6.91 (d, 1H); 8.71(d, 1H); 11.46 (s, 1H) 80 [CDCl3] 3.41 (s, 3H); 3.68 (s, 3H); 7.18 (d,1H); 8.32 (d, 1H) 81 [CDCl3] 4.50 (d, 2H); 5.3 (m, 2H); 6.0 (m, 1H);6.90 (d, 1H); 8.70 (d, 1H); 11.43 (s, 1H) 82 [CDCl3] 1.36 (s, 9H); 6.92(d, 1H); 8.72 (d, 1H); 11.22 (s, 1H); 13.0 (br, 1H) 92 [CDCl3] 4.62 (d,2H), 6.84 (d, 1H); 7.3 (m, 5H); 8.70 (d, 1H); 9.65 (br, 1H), 13.0 (br,1H) 93 [CDCl3] 2.95 (s, 3H); 4.65 (br, 2H); 7.05 (d, 1H); 7.3 (m, 5H),7.82 (d, 1H); 11.7 (br) 94 [DMSO] 4.55 (d, 2H); 7.33 (d, 1H); 7.37 (dd,1H); 7.75 (dt, 1H); 8.40 (d, 1H); 8.48 (dd, 1H); 8.58 (s, 1H); 9.45 (br,1H); 13.4 (br, 1H) 95 [DMSO] 4.55 (d, 2H); 7.30 (d, br, 1H); 7.50 (d,1H); 7.80 (dd, 1H); 8.37 (m, 2H); 9.55 (br, 1H); 13.4 (br, 1H) 96[CDCl3] 1.59 (d, 3H); 5.25 (m, 1H); 6.88 (d, 1H); 7.2-7.4 (m, 5H); 8.68(d, 1H); 9.75 (d, br, 1H); 13.5 (br, 1H) 97 [CDCl3] 2.94 (t, 2H); 3.70(m, 2H); 6.85 (d, 1H); 7.2-7.4 (m, 5H); 8.62 (d, 1H); 9.24 (br, 1H) 98[CDCl3] 4.81 (d, 2H); 6.85 (d, 1H); 7.40 (t, 1H); 7.52 (t, 1H); 7.61 (d,1H); 7.67 (d, 1H); 8.68 (d, 1H); 9.68 (t, br, 1H) 99 [DMSO] 2.28 (q,2H); 3.20 (q, 2H); 4.03 (t, 1H); 7.1-7.4 (m, 11H); 8.35 (d, 1H); 9.0(br), 13.4 (br, 1H) 100 [CDCl3] 3.45-3.55 (br, 4H); 3.75 (m, 4H); 7.03(d, 1H); 7.80 (d, 1H); 11.3 (br, 1H) 101 [CDCl3] 1.65 (m, 6H); 3.52 (m,4H); 7.10 (d, 1H); 7.72 (d, 1H) 102 [CDCl3] 3.06 (t, 2H); 3.90 (m, 2H);4.65 (m, 2H); 7.08 (d, 1H); 7.90 (d, 1H); 11.0 (br) 103 [CDCl3] 2.00 (m,4H); 3.67 (m, 4H); 7.20 (d, 1H); 7.97 (d, 1H), 11.7 (br, 1H) 104 [CDCl3]1.30 (m, 3H); 1.65 (m, 1H); 1.85 (m, 1H); 2.00 (m, 1H); 2.19 (m, 1H);3.62 (m, 2H); 4.30 (m, 1H); 7.10 (d, 1H); 7.89 (d, 1H) 105 [CDCl3] 3.25(s, 3H); 3.35 (3.3H); 7.25 (d, 1H); 8.58 (d, 1H); 8.76 (s, 1H) 112[CDCl3] 1.95 (m, 1H); 2.65 (m, 1H); 2.90 (m, 1H); 3.05 (m, 1H); 5.60 (m,1H); 6.85 (d, 1H); 7.2-7.4 (m, 4H); 8.68 (d, 1H); 9.52 (d, br, 1H) 113[CDCl3] 1.60 (m, 1H), 1.90 (m, 2H), 2.01 (m, 1H); 3.42 (m, 1H),3.65-3.82 (m, 2H), 3.90 (m, 1H), 4.09 (m, 1H); 6.88 (d, 1H); 8.63 (d,1H); 9.37 (br, 1H) 114 [DMSO] 7.35 (d, 1H); 8.10 (br, 1H); 8.40 (d, 1H);8.41 (br, 1H); 13.6 (br, 1H) 115 [CDCl3] 3.01 (d, 3H); 6.81 (d, 1H);8.63 (d, 1H); 9.22 (br, 1H); 11.7 (br, 1H) 116 [CDCl3] 1.25 (t, 3H); 3.5(m, 2H); 6.85 (d, 1H); 8.66 (d, 1H), 9.33 (br, 1H), 13.0 (br, 1H) 117[CDCl3] 1.01 (t, 3H); 1.62 (m, 2H); 3.42 (m, 2H); 6.86 (d, 1H); 8.66 (d,1H); 9.35 (br, 1H); 12.6 (br, 1H) 118 [CDCl3] 1.27 (d, 6H); 4.25 (m,1H); 6.85 (d, 1H); 8.64 (d, 1H); 9.27 (br, 1H); 13.1 (br, 1H) 119[CDCl3] 0.62 (m, 2H); 0.85 (m, 2H); 3.02 (m, 1H); 6.84 (d, 1H); 8.78 (d,1H), 9.33 (br, 1H) 120 [CDCl3] 0.98 (t, 3H); 1.41 (m, 2H); 1.61 (m, 2H);3.45 (q, 2H); 6.83 (d, 1H); 8.65 (d, 1H); 9.33 (br, 1H); 12.9 (br, 1H)121 [CDCl3] 1.80 (m, 2H); 2.05 (m, 2H); 2.44 (m, 2H); 4.58 (m, 1H); 6.84(d, 1H); 8.63 (d, 1H); 9.60 (br, 1H); 13.1 (br) 122 [CDCl3] 1.46 (s,9H); 6.86 (d, 1H); 8.62 (d, 1H); 9.34 (br, 1H); 13.4 (br, 1H) 123[CDCl3] 3.08 (s, 6H); 7.06 (d, 1H); 7.79 (d, 1H) 124 [CDCl3] 1.23 (t,3H); 3.04 (s, 3H); 3.46 (m, 2H); 7.02 (d, 1H); 7.72 (d, 1H) 125 [CDCl3]0.92 (t, 3H); 1.30 (br, 2H); 1.60 (m, 2H); 3.04 (s, 3H); 3.41 (br, 2H);7.04 (d, 1H); 7.71 (d, 1H) 127 [CDCl3] 1.20 (d, 6H); 2.90 (s, 3H); 4.05(m, br, 1H); 7.00 (d, 1H); 7.68 (d, 1H) 128 [CDCl3] 1.20 (t, 6H); 3.41(m, 4H); 6.98 (d, 1H); 7.66 d, 1H); 11.0 (br) 130 [CDCl3] 1.20 (m, 9H);3.40 (q, 2H); 4.06 (m, br, 1H); 6.98 (d, 1H); 8.64 (d, 1H); 10.2 (br)132 [CDCl3] 1.5-1.8 (m, 8H); 4.40 (m, 1H); 6.85 (d, 1H); 8.65 (d, 1H);9.40 (d, br, 1H); 13.1 (br, 1H) 133 [CDCl3] 1.2-1.7 (m, 6H); 1.80 (m,2H); 2.00 (m, 2H); 3.98 (m, 1H); 6.85 (d, 1H); 8.64 (d, 1H); 9.30 (d,br, 1H); 13.0 (br) 134 [CDCl3] 0.90 (t, 3H); 1.40 (m, 4H); 1.62 (m, 2H);3.44 (m, 2H); 6.84 (d, 1H); 8.64 (d, 1H); 9.30 (br, 1H) 136 [CDCl3] 0.30(m, 2H); 0.59 (m, 2H); 1.05 (m, 1H); 3.32 (m, 2H); 6.86 (d, 1H), 8.65(d, 1H); 9.40 (br) 138 [CDCl3] 1.00 (s, 9H); 3.26 (d, 2H); 6.86 (d, 1H);8.70 (d, 1H); 9.42 (br, 1H); 12.5 (br, 1H) 139 [DMSO] 4.25 (dt, 2H);7.25 (d, 1H); 8.40 (d, 1H); 9.35 (br, 1H); 13.5 (br, 1H) 140 [CDCl3]4.15 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H); 9.80 (br, 1H) 141 [CDCl3] 4.20(dt; 2H); 6.90 (d, 1H); 8.70 (d, 1H); 9.83 (t, br, 1H); 12.80 (br) 144[CDCl3] 1.00 (d, 6H); 1.90 (m, 1H); 3.30 (t, 2H); 6.83 (d, 1H); 8.65 (d,1H); 9.35 (br, 1H); 12.2 (br) 146 [CDCl3] 0.96 (d, 6H); 1.50 (m, 2H);1.70 (m, 1H); 3.48 (m, 2H); 6.83 (d, 1H); 8.67 (d, 1H); 9.30 (br, 1H),12.9 (br, 1H) 148 [CDCl3] 4.62 (d, 2H); 5.36 (dd, 2H); 5.95 (m, 1H);7.80 (d, 1H); 8.65 (d, 1H) 150 [CDCl3] 4.0 (m, 4H); 5.22 (d, 4H); 5.80(m, 2H); 6.93 (d, 1H); 7.72 (d, 1H) 152 [CDCl3] 1.80 (s, 3H); 4.02 (d,2H); 4.90 (d, 2H); 6.85 (d 1H); 8.68 (d, 1H); 9.48 (br, 1H); 12.8 (br,1H) 153 [CDCl3] 2.26 (t, 1H); 4.23 (m, 2H); 6.84 (d, 1H); 8.64 (d, 1H);9.58 (br, 1H); 12.4 (br) 154 [CDCl3] 2.30 (s, 1H); 3.12 (s, 3H); 4.24(br, 2H); 7.01 (d, 1H); 7.82 (d, 1H); 10.9 (br) 155 [CDCl3] 0.98 (t,3H); 1.22 (d, 3H); 1.59 (m, 2H); 4.10 (m, 1H); 6.85 (d, 1H); 8.65 (d,1H); 9.26 (d, br, 1H); 13.4 (br, 1H) 157 [CDCl3] 0.92 (t, 3H); 1.22 (d,3H); 1.40 (m, 2H); 1.55 (m, 2H); 4.20 (m, 1H); 6.85 (d, 1H); 8.68 (d,1H); 9.30 (d, br, 1H) 158 [CDCl3] 0.87 (t, 3H); 1.12 (d, 3H); 1.30 (m,4H); 1.58 (m, 4H); 4.15 (m, 1H); 6.84 (d, 1H); 8.65 (d, 1H); 9.24 (br,1H), 13.1 (br) 161 [CDCl3] 0.90 (d, 6H); 1.22 (d, 3H), 1.30 (m, 1H);1.55 (m, 2H); 4.23 (m, 1H); 6.86 (d, 1H); 8.64 (d, 1H); 9.20 (d, br,1H); 13.0 (br, 1H) 162 [CDCl3] 0.98 (s, 9H); 1.20 (d, 3H); 4.10 (m, 1H);6.87 (d, 1H); 8.70 (d, 1H); 9.38 (d, br, 1H), 13.2 (br, 1H) 163 [CDCl3]0.95 (dt, 6H); 1.20 (d, 3H); 1.82 (m, 1H); 4.05 (m, 1H); 6.84 (d, 1H);8.68 (d, 1H); 9.30 (d, br, 1H); 13.1 (br) 165 [CDCl3] 0.96 (t, 6H); 1.50(m, 2H); 1.65 (m, 2H); 4.00 (m, 1H); 6.85 (d, 1H); 8.68 (d, 1H); 9.22(d, br, 1H); 13.5 (br, 1H) 166 [CDCl3] 0.90 (t, 3H); 1.41 (s; 6H); 1.85(q, 2H); 6.82 (d, 1H); 8.61 (d, 1H); 9.20 (br, 1H); 13.1 (br) 168[CDCl3] 3.40 (s, 6H); 3.63 (t, 2H); 4.50 (t, 1H); 6.85 (d, 1H); 8.65 (d,1H); 9.40 (br, 1H); 12.4 (br, 1H) 169 [CDCl3] 1.21 (t, 6H); 3.60 (m,4H); 3.74 (m, 2H); 4.62 (t, 1H); 6.84 (d, 1H); 8.60 (d, 1H); 9.35 (br,1H), 11.5 (br) 171 [CDCl3] 3.40 (s, 3H); 3.58 (m, 2H); 3.67 (m, 2H);6.84 (d, 1H), 8.62 (d, 1H); 9.40 (br, 1H) 178 [CDCl3] 1.24 (d, 3H); 3.40(s, 3H); 3.42 (d, 2H); 4.40 (m, 1H); 6.86 (d, 1H); 8.64 (d, 1H); 9.35(br, 1H); 13.0 (br) 180 [DMSO] 1.75 (m, 2H); 3.22 (s, 3H); 3.36 (m, 4H);7.3 (br, 1H); 8.4 (d, 1H); 9.0 (br); 13.4 (br, 1H) 185 [DMSO] 3.65 (s,3H); 4.12 (d, 2H); 7.28 (d, br, 1H); 8.42 (d, 1H); 9.25 (t, br, 1H),13.6 (br, 1H) 189 [CDCl3] 2.66 (t, 2H); 3.70 (s, 3H); 3.76 (m, 2H); 6.83(d, 1H); 8.61 (d, 1H); 9.51 (t, br, 1H); 12.4 (br, 1H) 193 [CDCl3] 1.37(t, 3H); 4.08 (q, 2H); 6.88 (d, 1H); 8.69 (d, 1H); 11.48 (s, 1H) 194[CDCl3] 3.88 (s, 3H); 6.88 (d, 1H); 8.65 (d, 1H); 11.5 (s, 1H) 195[CDCl3] 4.50 (d, 2H); 5.34 (m, 2H); 6.05 (m, 1H); 6.88 (d, 1H); 8.70 (d,1H); 11.44 (s, 1H) 196 [CDCl3] 1.39 (s, 9H); 6.88 (d, 1H); 8.70 (d, 1H);11.22 (s, 1H) 206 [CDCl3] 4.62 (d, 2H), 6.82 (d, 1H); 7.2-7.3 (m, 5H);8.68 (d, 1H); 9.65 (t, br, 1H), 12.8 (br, 1H) 207 [CDCl3] 2.99 (s, 3H);4.67 (br, 2H); 7.00 (d, 1H); 7.3-7.4 (m, 5H), 7.78 (d, 1H); 10.2 (br)210 [CDCl3] 1.60 (d, 3H); 5.30 (m, 1H); 6.85 (d, 1H); 7.2-7.4 (m, 5H);8.65 (d, 1H); 9.78 (d, br, 1H); 13.2 (br, 1H) 211 [CDCl3] 2.95 (t, 2H);3.70 (m, 2H); 6.82 (d, 1H); 7.2-7.35 (m, 5H); 8.63 (d, 1H); 9.40 (t, br,1H); 12.2 (br, 1H) 214 [CDCl3] 3.45-3.55 (br, 4H); 3.75 (m, 4H); 6.96(d, 1H); 7.78 (d, 1H) 215 [CDCl3] 1.65 (m, 6H); 3.53 (m, 4H); 7.00 (d,1H); 7.70 (d, 1H) 216 [CDCl3] 3.05 (t, 2H); 3.92 (m, 2H); 4.66 (m, 2H);7.04 (d, 1H); 7.86 (d, 1H); 10.4 (br) 217 [CDCl3] 2.00 (m, 4H); 3.70 (m,4H); 7.16 (d, 1H); 7.97 (d, 1H), 11.7 (br, 1H) 218 [CDCl3] 1.30 (m, 3H);1.65 (m, 1H); 1.85 (m, 1H); 2.04 (m, 1H); 2.20 (m, 1H); 3.63 (m, 2H);4.33 (m, 1H); 7.12 (d, 1H); 7.89 (d, 1H), 11.5 (br, 1H) 227 [CDCl3] 1.60(m, 1H), 1.90 (m, 2H), 2.00 (m, 1H); 3.42 (m, 1H), 3.65-3.82 (m, 2H),3.90 (m, 1H), 4.10 (m, 1H); 6.88 (d, 1H); 8.65 (d, 1H); 9.5 (br, 1H) 228[DMSO] 6.80 (br, 1H); 6.90 (t, 1H); 7.72 (br, 1H); 8.40 (d, 1H); 8.90(br, 1H); 13.20 (br, 1H) 229 [DMSO] 2.82 (d, 3H); 6.75 (d, br, 1H); 6.90(t, 1H); 8.89 (d, 1H); 9.50 (br, 1H); 13.2 (br, 1H) 230 [DMSO] 1.11 (t,3H); 3.32 (m, 2H); 6.75 (d, br, 1H); 6.90 (t, 1H); 8.39 (d, 1H), 9.60(br, 1H), 13.2 (br, 1H) 232 [CDCl3] 1.25 (d, 6H); 4.22 (m, 1H); 6.55 (t,1H); 6.69 (d, 1H); 8.64 (d, 1H); 9.42 (d, br, 1H); 13.0 (br, 1H) 233[DMSO] 0.51 (m, 2H); 0.74 (m, 2H); 2.84 (m, 1H); 6.79 (d, br, 1H); 6.90(t, 1H); 8.37 (d, 1H); 9.65 (br, 1H); 13.1 (br, 1H) 250 [DMSO] 0.23 (m,2H); 0.46 (m, 2H); 1.02 (m, 1H); 3.20 (m, 2H); 6.75 (br, 1H), 6.92 (t,1H); 8.40 (d, 1H); 9.70 (br, 1H); 13.1 (br, 1H) 252 [DMSO] 0.91 (s, 9H);3.15 (d, 2H); 6.80 (br, 1H); 6.91 (t, 1H); 8.40 (d, 1H); 9.85 (br, 1H);13.2 (br, 1H) 258 [DMSO] 0.90 (d, 6H); 1.80 (m, 1H); 3.15 (t, 2H); 6.80(br, 1H); 6.91 (t, 1H); 8.40 (d, 1H); 9.73 (br, 1H); 13.1 (br, 1H) 262[DMSO] 3.96 (m, 2H); 5.15 (dd, 2H); 5.94 (m, 1H); 6.80 (br, 1H); 6.92(t, 1H); 8.40 (d, 1H); 9.75 (br, 1H); 13.2 (br, 1H) 271 [CDCl3] 0.92 (t,3H); 1.25 (d, 3H); 1.42 (m, 2H); 1.55 (m, 2H); 4.19 (m, 1H); 6.60 (t,1H); 6.73 (d, 1H); 8.66 (d, 1H); 9.50 (d, br, 1H) 272 [CDCl3] 0.90 (t,3H); 1.2-1.4 (m, 9H); 1.58 (m, 2H); 4.17 (m, 1H); 6.60 (t, 1H); 6.75 (d,1H); 8.68 (d, 1H); 9.48 (d, br, 1H) 279 [CDCl3] 0.85 (t, 6H); 1.45 (m,2H); 1.55 (m, 2H); 3.80 (m, 1H); 6.80 (br, 1H); 6.91 (t, 1H); 8.40 (d,1H); 9.51 (br, 1H); 13.1 (br, 1H) 280 [DMSO] 0.86 (t, 3H); 1.12 (d, 3H);1.50 (m, 2H); 3.90 (m, 1H); 6.75 (br, 1H); 6.91 (t, 1H); 8.39 (d, 1H);9.57 (br, 1H); 13.1 (br, 1H) 285 [DMSO] 3.29 (s, 3H); 3.46 (m, 4H); 6.76(br, 1H), 6.91 (t, 1H); 8.50 (d, 1H); 9.73 (br, 1H), 13.1 (br, 1H) 291[DMSO] 1.14 (d, 3H); 3.27 (s, 3H); 3.35 (m, 2H); 4.15 (m, 1H); 6.80 (br,1H); 6.91 (t, 1H); 8.40 (d, 1H); 9.70 (br, 1H); 13.1 (br, 1H)) 293[DMSO] 1.72 (m, 2H); 3.22 (s, 3H); 3.37 (m, 4H); 6.75 (br, 1H); 6.90 (t,1H); 8.40 (d, 1H); 9.70 (br, 1H)); 13.2 (br, 1H) 341 [DMSO] 7.45 (d,1H); 8.15 (br, 1H); 8.45 (br, 1H); 8.50 (d, 1H); 13.7 (br, 1H) 342[CDCl3] 3.01 (d, 3H); 6.90 (d, 1H); 8.72 (d, 1H); 9.34 (br, 1H) 343[DMSO] 1.11 (t, 3H); 3.31 (m, 2H); 7.41 (d, 1H); 8.42 (d, 1H); 8.85 (br,1H), 13.4 (br, 1H) 344 [CDCl3] 1.02 (t, 3H); 1.61 (m, 2H); 3.42 (q, 2H);6.88 (d, 1H); 8.72 (d, 1H); 9.38 (br, 1H) 345 [CDCl3] 1.25 (d, 6H); 4.25(m, 1H); 6.90 (d, 1H); 8.72 (d, 1H); 9.30 (d, br, 1H); 13.8 (br, 1H) 346[CDCl3] 0.60 (m, 2H); 0.88 (m, 2H); 3.02 (m, 1H); 6.90 (d, 1H); 8.72 (d,1H); 9.42 (br, 1H); 13.4 (br) 347 [DMSO] 0.88 (t, 3H); 1.34 (m, 2H);1.50 (m, 2H); 3.31 (q, 2H); 7.27 (d, 1H); 8.35 (d, 1H); 9.21 (br, 1H);12.4 (br, 1H) 348 [DMSO] 1.70 (m, 2H); 2.02 (m, 2H); 2.27 (m, 2H); 4.40(m, 1H); 7.41 (d, 1H); 8.48 (d, 1H); 9.00 (br, 1H); 13.4 (br, 1H) 349[DMSO] 1.36 (s, 9H); 7.35 (d, br, 1H); 8.40 (d, 1H); 8.60 (br, 1H); 13.3(br, 1H) 350 [CDCl3] 3.08 (s, 6H); 7.08 (d, 1H); 7.81 (d, 1H) 355[CDCl3] 1.21 (t, 6H); 3.42 (m, 4H); 7.04 (d, 1H); 7.71 (d, 1H); 10.8(br) 363 [DMSO] 0.27 (m, 2H); 0.46 (m, 2H); 1.05 (m, 1H); 3.15 (m, 2H);7.45 (d, br, 1H); 8.45 (d, 1H); 8.95 (br, 1H); 13.4 (br, 1H) 365 [DMSO]0.91 (s, 9H); 3.15 (d, 2H); 7.38 (d, br, 1H); 8.40 (d, 1H); 8.83 (br,1H); 13.4 (br, 1H) 373 [DMSO] 0.90 (d, 6H); 1.42 (m, 2H); 1.63 (m, 1H);3.33 (m, 2H); 7.40 (d, br, 1H); 8.40 (d, 1H); 8.83 (br, 1H), 13.4 (br,1H) 375 [DMSO] 3.95 (m, 2H); 5.15 (dd, 2H); 5.90 (m, 1H); 7.40 (d, 1H);8.41 (d, 1H); 8.98 (br, 1H); 13.4 (br, 1H) 379 [DMSO] 1.73 (s, 3H); 3.88(m, 2H); 4.75 (d, 2H); 7.40 (d, br, 1H); 8.41 (d, 1H); 8.97 (br, 1H);13.4 (br, 1H) 380 [DMSO] 3.15 (t, 1H); 4.21 (m, 2H); 7.40 (d, 1H); 8.40(d, 1H); 9.12 (br, 1H); 13.3 (br, 1H) 382 [CDCl3] 0.97 (t, 3H); 1.22 (d,3H); 1.59 (m, 2H); 4.10 (m, 1H); 6.88 (d, 1H); 8.72 (d, 1H); 9.24 (d,br, 1H); 13.6 (br) 384 [CDCl3] 0.92 (t, 3H); 1.21 (d, 3H); 1.40 (m, 2H);1.50 (m, 2H); 4.20 (m, 1H); 6.88 (d, 1H); 8.72 (d, 1H); 9.28 (d, br, 1H)385 [DMSO] 0.85 (t, 3H); 1.1-1.35 (m, 9H); 1.50 (m, 2H); 4.00 (m, 1H);7.41 (d, 1H); 8.40 (d, 1H); 8.65 (br, 1H); 13.4 (br, 1H) 388 [DMSO] 0.88(d, 6H); 1.15 (d, 3H), 1.28 (m, 1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.11(m, 1H); 7.40 (d, br, 1H); 8.40 (d, 1H); 8.52 (d, br, 1H); 13.4 (br, 1H)389 [DMSO] 0.90 (s, 9H); 1.10 (d, 3H); 3.90 (m, 1H); 7.38 (d, br, 1H);8.40 (d, 1H); 8.70 (br, 1H), 13.4 (br, 1H) 390 [DMSO] 0.79 (dt, 6H);1.10 (d, 3H); 1.75 (m, 1H); 3.87 (m, 1H); 7.40 (d, br, 1H); 8.41 (d,1H); 8.65 (d, br, 1H); 13.4 (br, 1H) 392 [CDCl3] 0.95 (t, 6H); 1.50 (m,2H); 1.65 (m, 2H); 4.00 (m, 1H); 6.90 (d, 1H); 8.75 (d, 1H); 9.20 (d,br, 1H); 13.7 (br, 1H) 395 [DMSO] 3.30 (s, 6H); 3.42 (t, 2H); 4.50 (t,1H); 7.40 (d, br, 1H); 8.45 (d, 1H); 8.90 (br, 1H); 13.4 (br, 1H) 397[DMSO] 3.38 (m, 2H); 3.52 (m, 2H); 4.80 (t, 1H); 7.40 (d, br, 1H); 8.43(d, 1H); 8.95 (br, 1H); 13.4 (br, 1H) 398 [CDCl3] 3.38 (s, 3H); 3.58 (m,2H); 3.65 (m, 2H); 6.88 (d, 1H), 8.70 (d, 1H); 9.43 (br, 1H) 405 [CDCl3]1.25 (d, 3H); 3.38 (s, 3H); 3.42 (d, 2H); 4.40 (m, 1H); 6.88 (d, 1H);8.70 (d, 1H); 9.38 (d, br, 1H) 407 [CDCl3] 1.89 (m, 2H); 3.32 (s, 3H);3.48 (t, 2H); 3.58 (m, 2H); 6.92 (d, 1H); 8.64 (d, 1H); 9.30 (br, 1H)455 [DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.50 (s, 1H); 13.8 (br, 1H) 456[DMSO] 2.84 (d, 3H); 8.40 (s, 1H); 8.72 (d, br, 1H) 457 [DMSO] 1.12 (t,3H); 3.35 (q, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H); 13.5 (br, 1H) 458[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.25 (m, 2H); 8.41 (s, 1H); 8.73 (t,br, 1H); 13.4 (br, 1H) 459 [DMSO] 1.19 (d, 6H); 4.08 (m, 1H); 8.43 (s,1H); 8.59 (d, br, 1H); 13.4 (br, 1H) 460 [DMSO] 0.59 (m, 2H); 0.75 (m,2H); 2.87 (m, 1H); 8.39 (s, 1H); 8.73 (d, br, 1H) 461 [DMSO] 0.90 (t,3H); 1.32 (m, 2H); 1.50 (m, 2H); 3.30 (m, 2H); 8.41 (s, 1H); 8.74 (t,br, 1H); 13.5 (br, 1H) 462 [DMSO] 1.70 (m, 2H); 2.03 (m, 2H); 2.25 (m,2H); 4.40 (m, 1H); 8.41 (s, 1H); 8.90 (d, br, 1H); 13.5 (br, 1H) 477[DMSO] 0.25 (m, 2H); 0.47 (m, 2H); 1.02 (m, 1H); 3.19 (t, 2H); 8.45 (s,1H); 8.80 (t, br, 1H) 479 [DMSO] 0.90 (s, 9H); 3.14 (d, 2H); 8.38 (s,1H); 8.60 (t, br, 1H); 13.7 (br, 1H) 485 [DMSO] 0.89 (d, 6H); 1.82 (m,1H); 3.13 (t, 2H); 8.40 (s, 1H); 8.72 (t, br, 1H) 487 [DMSO] 0.90 (d,6H); 1.41 (q, 2H); 1.62 (m, 1H); 3.32 (m, 2H); 8.40 (s, 1H); 8.72 (t,br, 1H); 13.5 (br, 1H) 489 [CDCl3] 4.10 (d, 2H); 5.25 (dd, 2H); 5.93 (m,1H); 8.60 (s, 1H); 9.10 (br, 1H); 12.4 (br, 1H) 493 [DMSO] 1.71 (s, 3H);3.86 (d, 2H); 4.84 (d, 2H); 8.40 (s, 1H); 8.85 (t, br, 1H); 13.5 (br)494 [DMSO] 3.17 (m, 1H); 4.11 (m, 2H); 8.39 (s, 1H); 8.98 (t, br, 1H),13.4 (br) 496 [CDCl3] 0.95 (t, 3H); 1.25 (d, 3H); 1.60 (m, 2H); 4.12 (m,1H); 8.48 (s, 1H); 8.52 (br, 1H) 498 [CDCl3] 0.95 (t, 3H); 1.25 (d, 3H);1.40 (m, 2H); 1.55 (m, 2H); 4.17 (m, 1H); 8.53 (s, 1H); 8.70 (br, 1H)499 [CDCl3] 0.87 (t, 3H); 1.21 (d, 3H); 1.32 (m, 6H); 1.53 (m, 2H); 4.15(m, 1H); 8.62 (s, 1H); 8.99 (d, br, 1H); 13.0 (br) 502 [CDCl3] 0.91 (d,6H); 1.23 (d, 3H); 1.35 (m, 1H); 1.48 (m, 1H); 1.66 (m, 1H); 4.25 (m,1H); 8.62 (s, 1H); 8.96 (d, br, 1H); 12.9 (br, 1H) 504 [CDCl3] 0.95 (m,6H); 1.18 (d, 3H); 1.81 (m, 1H); 4.07 (m, 1H); 8.61 (s, 1H); 8.97 (d,br, 1H); 12.9 (br, 1H) 506 [CDCl3] 0.94 (t, 6H); 1.50 (m, 2H); 1.65 (m,2H), 4.00 (m, 1H); 8.56 (s, 1H); 8.73 (d, br, 1H) 512 [DMSO] 3.28 (s,3H); 3.48 (m, 4H); 8.42 (s, 1H); 8.78 (br, 1H); 13.7 (br, 1H) 519 [DMSO]1.16 (d, 3H); 3.30 (s, 3H); 3.42 (m, 2H); 4.18 (m, 1H); 8.42 (s, 1H);8.60 (d, br, 1H); 13.7 (br, 1H) 521 [DMSO] 1.74 (m, 2H); 3.26 (s, 3H);3.39 (m, 4H); 8.40 (s, 1H); 8.80 (t, br, 1H); 13.6 (br, 1H) 569 [DMSO]8.25 (br, 1H); 8.35 (br, 1H); 8.50 (s, 1H); 13.7 (br, 1H) 570 [DMSO]2.82 (d, 3H); 8.40 (s, 1H); 8.71 (br, 1H); 13.5 (br, 1H) 571 [DMSO] 1.12(t, 3H); 3.35 (q, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H); 13.7 (br, 1H) 572[DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.26 (m, 2H); 8.39 (s, 1H); 8.82 (br,1H) 573 [DMSO] 1.18 (d, 6H); 4.09 (m, 1H); 8.42 (s, 1H); 8.53 (d, br,1H); 13.5 (br, 1H) 574 [DMSO] 0.59 (m, 2H); 0.74 (m, 2H); 2.85 (m, 1H);8.37 (s, 1H); 8.72 (d, br, 1H) 575 [DMSO] 0.89 (t, 3H); 1.35 (m, 2H);1.50 (m, 2H); 3.35 (m, 2H); 8.39 (s, 1H); 8.75 (br, 1H) 576 [DMSO] 1.70(m, 2H); 2.05 (m, 2H); 2.25 (m, 2H); 4.40 (m, 1H); 8.40 (s, 1H); 8.94(br, 1H) 591 [DMSO] 0.25 (m, 2H); 0.45 (m, 2H); 1.03 (m, 1H); 3.21 (t,2H); 8.40 (s, 1H); 8.84 (br, 1H) 599 [DMSO] 0.89 (d, 6H); 1.82 (m, 1H);3.14 (m, 2H); 8.38 (s, 1H); 8.74 (br, 1H) 601 [CDCl3] 0.96 (d, 6H); 1.51(m, 2H); 1.70 (m, 1H); 3.49 (m, 2H); 8.59 (s, 1H); 9.02 (br, 1H); 12.2(br) 603 [DMSO] 3.95 (t, 2H); 5.18 (dd, 2H); 5.89 (m, 1H); 8.40 (s, 1H);8.85 (t, br, 1H); 13.6 (br, 1H) 612 [CDCl3] 0.91 (t, 3H); 1.24 (d, 3H);1.40 (m, 2H); 1.54 (m, 2H); 4.18 (m, 1H); 8.57 (s, 1H); 8.90 (d, br,1H); 12.2 (br, 1H) 620 [CDCl3] 0.94 (t, 6H); 1.51 (m, 2H); 1.67 (m, 2H),3.99 (m, 1H); 8.57 (s, 1H); 8.82 (d, br, 1H) 626 [DMSO] 3.29 (s, 3H);3.48 (m, 4H); 8.41 (s, 1H); 8.78 (br, 1H); 13.7 (br, 1H) 633 [CDCl3]1.28 (d, 3H); 3.40 (s, 3H); 3.45 (m, 2H); 4.37 (m, 1H); 8.48 (s, 1H);8.78 (br, 1H) 635 [DMSO] 1.75 (m, 2H); 3.25 (s, 3H); 3.39 (m, 4H); 8.40(s, 1H); 8.81 (br, 1H); 13.6 (br, 1H) 797 [DMSO] 8.27 (br, 1H); 8.38(br, 1H); 8.52 (s, 1H); 13.7 (br, 1H) 798 [DMSO] 2.82 (d, 3H); 8.40 (s,1H); 8.75 (d, br, 1H); 13.6 (br, 1H) 799 [DMSO] 1.12 (t, 3H); 3.33 (m,2H); 8.41 (s, 1H); 8.78 (t, br, 1H); 13.6 (br, 1H) 800 [DMSO] 0.89 (t,3H); 1.52 (m, 2H); 3.27 (q, 2H); 8.41 (s, 1H); 8.76 (t, br, 1H); 13.5(br, 1H) 801 [DMSO] 1.18 (d, 6H); 4.09 (m, 1H); 8.42 (s, 1H); 8.60 (d,br, 1H) 802 [DMSO] 0.55 (m, 2H); 0.75 (m, 2H); 2.85 (m, 1H); 8.31 (s,1H); 9.24 (br, 1H); 13.4 (br, 1H) 803 [DMSO] 0.89 (t, 3H); 1.33 (m, 2H);1.51 (m, 2H); 3.30 (m, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H), 13.4 (br)804 [DMSO] 1.70 (m, 2H); 2.04 (m, 2H); 2.25 (m, 2H); 4.39 (m, 1H); 8.43(s, 1H); 8.95 (d, br, 1H); 13.4 (br, 1H) 806 [DMSO] 2.82 (s, 3H); 2.98(s, 3H); 8.06 (s, 1H); 12.6 (s, br, 1H) 811 [CDCl3] 1.24 (t, 6H); 3.44(m, 4H); 7.72 (s, 1H) 819 [DMSO] 0.25 (m, 2H); 0.46 (m, 2H); 1.03 (m,1H); 3.20 (t, 2H); 8.45 (s, 1H); 8.87 (t, br, 1H); 13.4 (br, 1H) 821[DMSO] 0.90 (s, 9H); 3.13 (d, 2H); 8.37 (s, 1H); 8.61 (t, br, 1H); 13.4(br, 1H) 827 [DMSO] 0.88 (d, 6H); 1.82 (m, 1H); 3.13 (t, 2H); 8.40 (s,1H); 8.76 (t, br, 1H); 13.5 (br, 1H) 829 [DMSO] 0.90 (d, 6H); 1.42 (m,2H); 1.61 (m, 1H); 3.30 (m, 2H); 8.41 (s, 1H); 8.76 (t, br, 1H); 13.5(br, 1H) 831 [DMSO] 3.95 (t, 2H); 5.19 (dd, 2H); 5.89 (m, 1H); 8.41 (s,1H); 8.88 (t, br, 1H), 13.5 (br, 1H) 835 [DMSO] 1.72 (s, 3H); 3.87 (d,2H); 4.86 (d, 2H); 8.39 (s, 1H); 8.90 (t, br, 1H); 13.4 (br, 1H) 836[DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.36 (s, 1H); 9.01 (t, br, 1H); 13.4(br, 1H) 838 [DMSO] 0.88 (t, 3H); 1.14 (d, 3H); 1.51 (m, 2H); 3.91 (m,1H); 8.41 (s, 1H); 8.54 (d, br, 1H); 13.5 (br, 1H) 840 [DMSO] 0.88 (t,3H); 1.14 (d, 3H); 1.33 (m, 2H), 1.47 (m, 2H); 4.01 (m, 1H); 8.42 (s,1H); 853 (d, br, 1H); 13.5 (br, 1H) 841 [DMSO] 0.85 (t, 3H); 1.14 (d,3H); 1.28 (m, 6H); 1.49 (m, 2H); 3.98 (m, 1H); 8.41 (s, 1H); 8.60 (d,br, 1H); 13.5 (br, 1H) 844 [DMSO] 0.87 (d, 6H); 1.14 (d, 3H); 1.27 (m,1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.09 (m, 1H); 8.41 (s, 1H); 8.52 (d,br, 1H); 13.5 (br, 1H) 845 [DMSO] 0.90 (s, 9H); 1.08 (d, 3H); 3.90 (m,1H); 8.35 (s, 1H); 8.38 (d, br, 1H); 13.4 (br) 846 [DMSO] 0.89 (d, 6H);1.12 (d, 3H); 1.75 (m, 1H); 3.87 (m, 1H); 8.40 (s, 1H); 8.50 (d, br,1H); 13.5 (br) 848 [DMSO] 0.87 (t, 6H); 1.44 (m, 2H); 1.55 (m, 2H), 3.79(m, 1H); 8.40 (s, 1H); 8.42 (d, br, 1H); 13.4 (br, 1H) 851 [CDCl3] 3.42(s, 6H); 3.63 (t, 2H); 4.50 (t, 1H); 8.55 (s, 1H); 8.95 (t, br, 1H);12.1 (br, 1H) 853 [CDCl3] 3.65 (m, 2H); 3.86 (m, 2H); 8.47 (s, 1H); 8.98(br, 1H) 854 [CDCl3] 3.39 (s, 3H); 3.58 (m, 2H); 3.69 (m, 2H); 8.49 (s,1H); 8.80 (br, 1H); 11.9 (br, 1H) 861 [CDCl3] 1.28 (d, 3H); 3.38 (s,3H); 3.45 (m, 2H); 4.39 (m, 1H); 8.51 (s, 1H); 8.85 (br, 1H); 12.4 (br,1H) 863 [CDCl3] 1.90 (m, 2H); 3.40 (s, 3H); 3.57 (m, 4H); 8.30 (s, 1H);8.70 (br, 1H) 868 [CDCl3] 3.80 (s, 3H); 4.25 (d, 2H); 8.52 (s, 1H); 9.16(br, 1H) 909 [DMSO] 8.22 (br, 1H); 8.32 (br, 1H); 8.61 (s, 1H); 13.8(br, 1H) 910 [DMSO] 2.83 (d, 3H); 8.51 (s, 1H); 8.74 (br, 1H); 13.7 (br,1H) 911 [DMSO] 1.12 (t, 3H); 3.32 (q, 2H); 8.54 (s, 1H); 8.75 (t, br,1H); 13.7 (br, 1H) 912 [DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.25 (q, 2H);8.54 (s, 1H); 8.75 (t, br, 1H); 13.6 (br, 1H) 913 [CDCl3] 1.25 (d, 6H);4.25 (m, 1H); 8.54 (br, 1H); 8.70 (s, 1H) 914 [DMSO] 0.58 (m, 2H); 0.75.(m, 2H); 2.86 (m, 1H); 8.50 (s, 1H); 8.75 (d, 1H); 13.6 (br, 1H) 915[DMSO] 0.89 (t, 3H); 1.32 (m, 2H); 1.50 (m, 2H); 3.32 (m, 2H); 8.53 (s,1H); 8.74 (t, br, 1H), 13.5 (br) 916 [DMSO] 1.70 (m, 2H); 2.05 (m, 2H);2.25 (m, 2H); 4.40 (m, 1H); 8.52 (s, 1H); 8.98 (d, br, 1H); 13.5 (br,1H) 917 [CDCl3] 1.50 (s, 9H); 8.65 (s, 1H); 8.80 (s, br, 1H); 12.3 (br,1H) 918 [DMSO] 2.82 (s, 3H); 2.99 (s, 3H); 8.14 (s, 1H); 12.6 (br, 1H)923 [DMSO] 1.02 (t, 3H); 1.12 (t, 3H); 3.10 (q, 2H); 3.40 (q, 2H); 8.15(s, 1H), 12.5 (br, 1H) 931 [DMSO] 0.24 (m, 2H); 0.46 (m, 2H); 1.04 (m,1H); 3.18 (t, 2H); 8.55 (s, 1H); 8.82 (t, br, 1H) 933 [DMSO] 0.90 (s,9H); 3.13 (d, 2H); 8.50 (s, 1H); 8.61 (t, br, 1H) 939 [DMSO] 0.88 (d,6H); 1.83 (m, 1H); 3.14 (t, 2H); 8.52 (s, 1H); 8.72 (t, br, 1H); 13.6(br, 1H) 941 [DMSO] 0.90 (d, 6H); 1.43 (m, 2H); 1.62 (m, 1H); 3.35 (m,2H); 8.52 (s, 1H); 8.72 (t, br, 1H); 13.5 (br, 1H) 943 [DMSO] 3.94 (t,2H); 5.18 (dd, 2H); 5.89 (m, 1H); 8.52 (s, 1H); 8.85 (t, br, 1H) 947[DMSO] 1.72 (s, 3H); 3.87 (d, 2H); 4.85 (d, 2H); 8.51 (s, 1H); 8.87 (t,br, 1H); 13.5 (br) 948 [DMSO] 3.18 (m, 1H); 4.12 (m, 2H); 8.50 (s, 1H);9.00 (t, br, 1H) 950 [DMSO] 0.92 (t, 3H); 1.21 (d, 3H); 1.57 (m, 2H);3.97 (m, 1H); 8.55 (d, br, 1H); 8.60 (s, 1H); 13.7 (br, 1H) 952 [CDCl3]0.90 (t, 3H); 1.24 (d, 3H); 1.40 (m, 2H), 1.55 (m, 2H); 4.18 (m, 1H);8.72 (s, 1H); 8.90 (d, br, 1H) 953 [DMSO] 0.77 (t, 3H); 1.15 (d, 3H);1.27 (m, 6H); 1.49 (m, 2H); 3.99 (m, 1H); 8.50 (d, br, 1H); 8.55 (s,1H); 13.6 (br) 956 [DMSO] 0.88 (d, 6H); 1.15 (d, 3H); 1.27 (m, 1H); 1.48(m, 1H); 1.62 (m, 1H); 4.10 (m, 1H); 8.50 (d, br, 1H); 8.55 (s, 1H);13.6 (br, 1H) 957 [DMSO] 0.91 (s, 9H); 1.09 (d, 3H); 3.80 (m, 1H); 8.39(d, br, 1H); 8.49 (s, 1H); 13.6 (br, 1H) 958 [DMSO] 0.89 (d, 6H); 1.11(d, 3H); 1.75 (m, 1H); 3.86 (m, 1H); 8.48 (d, br, 1H); 8.52 (s, 1H);13.6 (br) 960 [CDCl3] 0.95 (t, 6H); 1.50 (m, 2H); 1.62 (m, 2H), 4.00 (m,1H); 8.73 (s, 1H); 8.90 (d, br, 1H) 963 [CDCl3] 3.43 (s, 6H); 3.65 (t,2H); 4.50 (t, 1H); 8.62 (s, 1H); 8.78 (br, 1H) 965 [DMSO] 3.40 (m, 2H);3.52 (m, 2H); 8.57 (s, 1H); 8.78 (t, br, 1H); 13.6 (br, 1H) 966 [DMSO]3.29 (s, 3H); 3.48 (m, 4H); 8.54 (s, 1H); 8.78 (br, 1H); 13.6 (br, 1H)973 [CDCl3] 1.29 (d, 3H); 3.40 (s, 3H); 3.45 (m, 2H); 4.36 (m, 1H); 8.60(s, 1H); 8.72 (br, 1H) 975 [DMSO] 1.75 (m, 2H); 3.20 (s, 3H); 3.38 (m,4H); 8.51 (s, 1H); 8.81 (t, br, 1H); 13.6 (br) 1023 [DMSO] 8.22 (br,1H); 8.35 (br, 1H); 8.61 (s, 1H); 13.8 (br, 1H) 1024 [DMSO] 2.82 (d,3H); 8.50 (s, 1H); 8.75 (br, 1H); 13.7 (br, 1H) 1025 [DMSO] 1.13 (t,3H); 3.35 (m, 2H); 8.52 (s, 1H); 8.75 (br, 1H); 13.5 (br, 1H) 1026[DMSO] 0.90 (t, 3H); 1.53 (m, 2H); 3.25 (m, 2H); 8.52 (s, 1H); 8.75 (t,br, 1H); 13.5 (br, 1H) 1027 [DMSO] 1.18 (d, 6H); 4.08 (m, 1H); 8.54 (s,1H); 8.56 (br, 1H) 1028 [DMSO] 0.58 (m, 2H); 0.75 (m, 2H); 3.86 (m, 1H);8.48 (s, 1H); 8.75 (br, 1H) 1029 [DMSO] 0.89 (t, 3H); 1.34 (m, 2H); 1.50(m, 2H); 3.26 (m, 2H); 8.51 (s, 1H); 8.81 (br, 1H); 13.6 (br, 1H) 1030[DMSO] 1.70 (m, 2H); 2.04 (m, 2H); 2.25 (m, 2H); 4.39 (m, 1H); 8.53 (s,1H); 8.91 (d, br, 1H); 13.4 (br, 1H) 1031 [CDCl3] 1.46 (s, 9H); 8.63 (s,1H); 8.83 (br, 1H); 111.9 (br, 1H) 1032 [DMSO] 2.82 (s, br, 3H); 2.96(s, br, 3H); 8.11 (s, 1H); 12.5 (br, 1H) 1037 [CDCl3] 1.23 (t, 6H); 3.42(br, 4H); 7.88 (s, 1H) 1045 [DMSO] 0.25 (m, 2H); 0.46 (m, 2H); 1.04 (m,1H); 3.20 (t, 2H); 8.55 (s, 1H); 8.82 (t, br, 1H); 13.6 (br, 1H) 1047[DMSO] 0.90 (s, 9H); 3.13 (d, 2H); 8.48 (s, 1H); 8.61 (t, br, 1H) 1053[DMSO] 0.90 (d, 6H); 1.82 (m, 1H); 3.13 (m, 2H); 8.50 (s, 1H); 8.75 (br,1H); 13.5 (br, 1H) 1055 [DMSO] 0.89 (d, 6H); 1.41 (m, 2H); 1.61 (m, 1H);3.31 (m, 2H); 8.49 (s, 1H); 8.90 (br, 1H); 13.5 (br, 1H) 1057 [DMSO]3.95 (t, 2H); 5.18 (dd, 2H); 5.90 (m, 1H); 8.50 (s, 1H); 8.85 (t, br,1H) 1061 [CDCl3] 1.80 (s, 3H); 4.03 (d, 2H); 4.93 (d, 2H); 8.76 (s, 1H);9.22 (t, br, 1H); 1062 [DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.48 (s, 1H);9.00 (br, 1H) 1064 [DMSO] 0.88 (t, 3H); 1.16 (d, 3H); 1.51 (m, 2H); 3.93(m, 1H); 8.50 (d, br, 1H); 8.55 (s, 1H); 13.6 (br, 1H) 1066 [DMSO] 0.86(t, 3H); 1.15 (d, 3H); 1.30 (m, 2H), 1.48 (m, 2H); 4.00 (m, 1H); 8.50(d, br, 1H); 8.52 (s, 1H); 13.6 (br, 1H) 1067 [CDCl3] 0.86 (t, 3H); 1.22(d, 3H); 1.25 (m, 6H); 1.48 (m, 2H); 4.16 (m, 1H); 8.62 (s, 1H); 8.68(br, 1H) 1070 [CDCl3] 0.93 (d, 6H); 1.23 (d, 3H); 1.27 (m, 1H); 1.50 (m,1H); 1.70 (m, 1H); 4.25 (m, 1H); 8.63 (br, 2H) 1071 [CDCl3] 0.95 (s,9H); 1.17 (d, 3H); 4.08 (m, 1H); 8.70 (s, 1H); 9.00 (d, br, 1H) 1072[CDCl3] 0.95 (m, 6H); 1.20 (d, 3H); 1.82 (m, 1H); 4.07 (m, 1H); 8.76 (s,1H); 9.13 (br, 1H) 1074 [CDCl3] 0.92 (t, 6H); 1.50 (m, 2H); 1.65 (m,2H), 3.96 (m, 1H); 8.72 (s, 1H); 9.00 (d, br, 1H) 1077 [CDCl3] 3.42 (s,6H); 3.62 (t, 2H); 4.50 (t, 1H); 8.62 (s, 1H); 8.90 (br, 1H) 1079[CDCl3] 3.65 (m, 2H); 3.85 (m, 2H); 8.64 (s, 1H); 9.22 (br, 1H) 1080[DMSO] 3.30 (s, 3H); 3.46 (m, 4H); 8.52 (s, 1H); 8.75 (br, 1H) 1087[CDCl3] 1.29 (d, 3H); 3.39 (s, 3H); 3.45 (m, 2H); 4.37 (m, 1H); 8.66 (s,1H); 8.98 (br, 1H); 12.50 (br, 1H) 1089 [DMSO] 1.75 (m, 2H); 3.23 (s,3H); 3.38 (m, 4H); 8.52 (s, 1H); 8.80 (t, br, 1H) 1094 [CDCl3] 3.80 (s,3H); 4.24 (d, 2H); 8.61 (s, 1H); 9.19 (br, 1H) 1138 [DMSO] 2.83 (d, 3H);7.07 (t, 1H); 8.40 (s, 1H); 8.94 (br, 1H); 13.4 (br, 1H) 1139 [DMSO]1.12 (t, 3H); 3.33 (m, 2H); 7.08 (t, 1H); 8.40 (s, 1H); 9.00 (br, 1H);13.4 (br, 1H) 1171 [DMSO] 3.90 (t, 2H); 5.15 (dd, 2H); 5.90 (m, 1H);7.10 (t, 1H); 8.40 (s, 1H); 9.16 (br, 1H); 13.4 (br, 1H) 1178 [CDCl3]0.95 (t, 3H); 1.21 (d, 3H); 1.58 (m, 2H); 4.08 (m, 1H); 6.86 (t, 1H);8.70 (s, 1H); 9.34 (d, br, 1H); 12.9 (br, 1H) 1180 [CDCl3] 0.93 (t, 3H);1.21 (d, 3H); 1.40 (m, 2H); 1.52 (m, 2H); 4.16 (m, 1H); 6.87 (t, 1H);8.70 (s, 1H); 9.31 (d, br, 1H); 12.9 (br, 1H) 1188 [CDCl3] 0.92 (t, 6H);1.50 (m, 2H); 1.65 (m, 2H); 3.98 (m, 1H); 6.86 (t, 1H); 8.71 (s, 1H);9.28 (d, br, 1H); 12.9 (br, 1H) 1201 [CDCl3] 1.27 (d, 3H); 3.40 (s, 3H);3.43 (m, 2H); 4.37 (m, 1H); 6.85 (t, 1H); 8.68 (s, 1H); 9.42 (d, br,1H); 12.7 (br, 1H) 1251 [DMSO] 8.26 (br, 1H), 8.42 (br, 1H); 8.62 (s,1H) 1252 [CDCl3] 3.00 (d, 3H); 8.66 (s, 1H); 8.82 (br, 1H) 1253 [CDCl3]1.24 (t, 3H); 3.50 (m, 2H); 8.68 (s, 1H); 8.86 (br, 1H) 1254 [CDCl3]1.00 (t, 3H); 1.62 (m, 2H); 3.42 (m, 2H); 8.67 (s, 1H); 8.90 (br, 1H)1255 [CDCl3] 1.25 (d, 6H); 4.25 (m, 1H); 8.70 (s, 1H); 8.84 (br, 1H)1256 [CDCl3] 0.60 (m, 2H); 0.89. (m, 2H); 3.00 (m, 1H); 8.70 (s, 1H);9.00 (br, 1H) 1257 [CDCl3] 0.96 (t, 3H); 1.42. (m, 2H); 1.60 (m, 2H);3.45 (m, 2H); 8.70 (s, 1H); 8.88 (br, 1H); 12.1 (br, 1H) 1258 [CDCl3]1.77 (m, 2H); 1.98. (m, 2H); 2.43 (m, 2H); 4.55 (m, 1H); 8.68 (s, 1H);9.13 (br, 1H); 12.5 (br, 1H) 1259 [CDCl3] 1.45 (s, 9H); 8.67 (s, 1H);8.78 (br, 1H); 12.4 (br, 1H) 1260 [CDCl3] 3.11 (s, 6H); 7.95 (s, 1H)1265 [CDCl3] 1.25 (t, 6H); 3.45 (br, 4H); 7.89 (s, 1H) 1273 [CDCl3] 0.27(m, 2H); 0.56. (m, 2H); 1.04 (m, 1H); 3.32 (m, 2H); 8.67 (s, 1H); 8.92(br, 1H); 12.3 (br, 1H) 1275 [CDCl3] 0.97 (s, 9H); 3.29 (d, 2H); 8.73(s, 1H); 9.00 (br, 1H); 11.9 (br, 1H) 1281 [CDCl3] 0.98 (d, 6H); 1.89(m, 1H); 3.29 (t, 2H); 8.70 (s, 1H); 8.98 (br, 1H); 12.1 (br, 1H) 1283[CDCl3] 0.95 (d, 6H); 1.50 (m, 2H); 1.68 (m 1H); 3.46 (m, 2H); 8.69 (s,1H); 8.83 (br, 1H); 12.1 (br, 1H) 1285 [CDCl3] 4.09 (t, 2H); 5.22 (dd,2H); 5.91 (m, 1H); 8.70 (s, 1H); 9.01 (br, 1H); 12.2 (br, 1H) 1289[DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.05 (m, 1H); 3.20 (m, 2H); 6.85 (tt,1H); 7.25 (br, 1H); 8.45 (d, 1H); 9.15 (br, 1H), 13.4 (br, 1H) 1290[CDCl3] 2.25 (m, 1H); 4.23 (m, 2H); 8.72 (s, 1H); 9.20 (br, 1H), 12.0(br, 1H) 1292 [CDCl3] 0.95 (t, 3H); 1.21 (d, 3H); 1.55 (m 2H); 4.10 (m,1H); 8.70 (s, 1H); 8.82 (br, 1H) 1294 [CDCl3] 0.93 (t, 3H); 1.22 (d,3H); 1.38 (m, 2H); 1.52 (m 2H); 4.18 (m, 1H); 8.70 (s, 1H); 8.79 (br,1H); 12.4 (br, 1H) 1295 [CDCl3] 0.89 (t, 3H); 1.20 (d, 3H); 1.25-1.4 (m,6H); 1.50 (m, 2H); 4.16 (m, 1H); 8.70 (s, 1H); 8.75 (br, 1H) 1298[CDCl3] 0.92 (t, 6H); 1.40 (d, 3H); 1.32 (m, 1H); 1.45 (m, 1H); 1.55 (m,1H); 4.25 (m, 1H); 8.70 (s, 1H); 8.75 (br, 1H); 12.4 (br, 1H) 1299[CDCl3] 0.95 (s, 9H); 1.15 (d, 3H); 4.10 (m, 1H); 8.72 (s, 1H); 8.88(br, 1H); 11.9 (br, 1H) 1300 [CDCl3] 0.95 (m, 6H); 1.15 (d, 3H); 1.77(m, 1H); 4.05 (m, 1H); 8.71 (s, 1H); 8.85 (br, 1H) 1302 [CDCl3] 0.93 (t,6H); 1.48 (m, 2H); 1.65 (m, 2H); 3.99 (m, 1H); 8.71 (s, 1H); 8.76 (br,1H); 12.4 (br, 1H) 1305 [CDCl3] 3.40 (s, 6H); 3.62 (t, 2H); 4.50 (t,1H); 8.60 (s, 1H); 8.74 (br, 1H); 11.7 (br, 1H) 1307 [CDCl3] 3.65 (m,2H); 3.87 (m, 2H); 4.50 (t, 1H); 8.66 (s, 1H); 9.11 (br, 1H) 1308[CDCl3] 3.40 (s, 3H); 3.58 (m, 2H); 3.67 (m, 2H); 8.60 (s, 1H); 8.75(br, 1H); 11.7 (br, 1H) 1315 [CDCl3] 1.48 (d, 3H); 3.38 (s, 3H); 3.44(m, 2H); 4.38 (m, 1H); 8.62 (s, 1H); 8.72 (br, 1H); 12.1 (br, 1H) 1317[CDCl3] 1.90 (m, 2H); 3.40 (s, 3H); 3.58 (m, 4H); 8.39 (s, 1H); 8.62(br, 1H) 1322 [CDCl3] 3.79 (s, 3H); 4.25 (d, 2H); 8.65 (s, 1H); 9.18(br, 1H) 1365 [DMSO] 8.24 (br, 1H), 8.42 (br, 1H); 8.81 (s, 1H); 13.6(br, 1H) 1366 [DMSO] 8.19 (br, 1H), 8.34 (br, 1H); 8.78 (s, 1H); 13.7(br, 1H) 1368 [DMSO] 2.83 (d, 3H); 6.81 (tt, 1H); 7.22 (br, 1H); 8.41(d, 1H); 9.00 (br, 1H); 13.4 (br, 1H) 1369 [DMSO] 1.12 (t, 3H); 3.35 (m,2H); 6.85 (tt, 1H); 7.20 (br, 1H); 8.41 (d, 1H); 9.20 (br, 1H); 13.4(br, 1H) 1370 [DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.27 (q, 2H); 6.82 (tt,1H); 7.20 (br, 1H); 8.40 (d, 1H); 9.20 (br, 1H); 13.4 (br, 1H) 1371[DMSO] 1.18 (d, 6H); 4.09 (m, 1H); 6.82 (tt, 1H); 7.20 (br, 1H); 8.42(d, 1H); 8.95 (br, 1H); 13.4 (br, 1H) 1372 [DMSO] 0.56 (m, 2H); 0.75 (m,2H); 2.85 (m, 1H); 6.83 (tt, 1H); 7.21 (br, 1H); 8.40 (d, 1H); 9.05 (br,1H); 13.4 (br, 1H) 1373 [DMSO] 0.89 (t, 3H); 1.32 (m, 2H); 1.50 (m, 2H);3.30 (q, 2H); 6.84 (tt, 1H); 7.20 (br, 1H); 8.41 (d, 1H); 9.10 (br, 1H);13.4 (br, 1H) 1389 [DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.05 (m, 1H); 3.20(m, 2H); 6.85 (tt, 1H); 7.25 (br, 1H); 8.45 (d, 1H); 9.15 (br, 1H), 13.4(br, 1H) 1391 [DMSO] 0.91 (s, 9H); 3.16 (d, 2H); 6.82 (tt, 1H); 7.10(br, 1H); 8.41 (d, 1H); 9.20 (br, 1H); 13.3 (br, 1H) 1397 [DMSO] 0.90(d, 6H); 1.82 (m, 1H); 3.15 (m, 2H); 6.82 (tt, 1H); 7.20 (br, 1H); 8.40(d, 1H); 9.15 (br, 1H), 13.4 (br, 1H) 1401 [DMSO] 3.95 (m, 2H); 5.18(dd, 2H); 5.92 (m, 1H); 6.82 (tt, 1H); 7.20 (d, 1H); 8.42 (d, 1H); 9.20(br, 1H); 13.3 (br, 1H) 1406 [DMSO] 3.15 (t, 1H); 4.13 (m, 2H); 6.82(tt, 1H); 7.18 (br, 1H); 8.41 (d, 1H); 9.35 (br, 1H); 13.3 (br, 1H) 1408[DMSO] 0.87 (t, 3H); 1.14 (d, 3H); 1.51 (m, 2H); 3.92 (m, 1H); 6.82 (tt,1H); 7.20 (br, 1H); 8.41 (d, 1H); 8.90 (br, 1H), 13.4 (br, 1H) 1410[DMSO] 0.86 (t, 3H); 1.15 (d, 3H); 1.30 (m, 2H); 1.48 (m, 2H); 4.02 (m,1H); 6.83 (tt, 1H); 7.20 (br, 1H); 8.42 (d, 1H); 8.90 (br, 1H), 13.4(br, 1H) 1411 [DMSO] 0.88 (t, 3H); 1.15 (d, 3H); 1.27 (m, 6H); 1.49 (m,2H); 4.00 (m, 1H); 6.82 (tt, 1H); 7.20 (br, 1H); 8.42 (d, 1H); 8.92 (br,1H), 13.4 (br, 1H) 1414 [DMSO] 0.88 (d, 6H); 1.15 (d, 3H); 1.28 (m, 1H);1.46 (m, 1H); 1.60 (m, 1H); 4.10 (m, 1H); 6.81 (tt, 1H); 7.20 (br, 1H);8.42 (d, 1H); 8.90 (br, 1H), 13.4 (br, 1H) 1418 [CDCl3] 0.93 (t, 6H);1.50 (m, 2H); 1.65 (m, 2H); 4.00 (m, 1H); 6.83 (d, 1H); 8.69 (d, 1H);9.21 (d, br, 1H); 13.0 (br, 1H) 1421 [CDCl3] 3.41 (s, 6H); 3.52 (t, 2H);4.50 (t, 1H); 6.12 (tt, 1H); 6.81 (d, 1H); 8.64 (d, 1H); 9.41 (br, 1H);12.5 (br, 1H) 1424 [CDCl3] 3.37 (s, 3H); 3.56 (m, 2H); 3.67 (m, 2H);6.11 (tt, 1H); 6.84 (d, 1H); 8.65 (d, 1H); 9.46 (br, 1H), 12.2 (br, 1H)1431 [CDCl3] 1.28 (d, 3H); 3.39 (s, 3H); 3.45 (m, 2H); 4.40 (m, 1H);6.10 (tt, 1H); 6.83 (d, 1H); 8.67 (d, 1H); 9.39 (d, br, 1H); 13.0 (br,1H) 1433 [DMSO] 1.75 (m, 2H); 3.24 (s, 3H); 3.38 (m, 4H); 6.83 (tt, 1H);7.20 (br, 1H); 8.42 (d, 1H); 9.15 (br, 1H), 13.4 (br, 1H) 1481 [DMSO]7.42 (br, 1H); 8.10 (br, 1H); 8.40 (br, 1H); 8.46 (d, 1H), 13.6 (br, 1H)1482 [CDCl3] 3.01 (d, 3H); 6.88 (d, 1H); 8.67 (d, 1H); 9.34 (br, 1H);12.5 (br, 1H) 1483 [CDCl3] 1.27 (t, 3H); 3.50 (m, 2H); 6.88 (d, 1H);8.68 (d, 1H); 9.32 (br, 1H); 12.6 (br, 1H) 1484 [CDCl3] 1.00 (t, 3H);1.63 (m, 2H); 3.41 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H); 9.38 (br, 1H);12.9 (br, 1H) 1485 [CDCl3] 1.25 (d, 6H); 4.27 (m, 1H); 6.88 (d, 1H);8.70 (d, 1H); 9.30 (d, br, 1H); 13.4 (br, 1H) 1486 [CDCl3] 0.62 (m, 2H);0.86 (m, 2H); 3.01 (m, 1H); 6.88 (d, 1H); 8.70 (d, 1H); 9.41 (br, 1H);12.6 (br, 1H) 1487 [CDCl3] 0.95 (t, 3H); 1.44 (m, 2H); 1.61 (m, 2H);3.45 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H); 9.35 (t, br, 1H); 12.7 (br,1H) 1488 [CDCl3] 1.78 (m, 2H); 2.00 (m, 2H); 2.42 (m, 2H); 4.58 (m, 1H);6.88 (d, 1H); 8.68 (d, 1H); 9.60 (d, br, 1H); 13.3 (br, 1H) 1503 [CDCl3]0.26 (m, 2H); 0.55 (m, 2H); 1.06 (m, 1H); 3.33 (m, 2H); 6.88 (d, 1H);8.70 (d, 1H); 9.45 (br, 1H); 12.9 (br, 1H) 1505 [CDCl3] 0.98 (s, 9H);3.30 (d, 2H); 6.88 (d, 1H); 8.72 (d, 1H); 9.43 (t, br, 1H); 12.5 (br,1H) 1511 [CDCl3] 0.98 (d, 6H); 1.90 (m, 1H); 3.30 (m, 2H); 6.88 (d, 1H);8.70 (d, 1H); 9.42 (t, br, 1H) 1513 [CDCl3] 0.85 (d, 6H); 1.51 (m, 2H);1.70 (m, 1H); 3.47 (m, 2H); 6.88 (d, 1H); 8.70 (d, 1H); 9.32 (t, br,1H); 12.7 (br, 1H) 1515 [CDCl3] 4.10 (t, 2H); 5.25 (dd, 2H); 5.91 (m,1H); 6.88 (d, 1H); 8.70 (d, 1H); 9.47 (br, 1H); 12.8 (br, 1H) 1519[DMSO] 1.71 (s, 3H); 3.88 (d, 2H); 4.84 (d, 2H); 7.35 (br, 1H); 8.41 (d,1H); 9.02 (br, 1H); 13.4 (br, 1H) 1520 [DMSO] 3.15 (m, 1H); 4.12 (m,2H); 7.36 (d, br, 1H); 8.42 (d, 1H); 9.15 (br, 1H), 13.4 (br, 1H) 1522[CDCl3] 0.95 (t, 3H); 1.22 (d, 3H); 1.59 (m, 2H); 4.11 (m, 1H); 6.88 (d,1H); 8.71 (d, 1H); 9.28 (d, br, 1H); 13.4 (br, 1H) 1524 [CDCl3] 0.92 (t,3H); 1.23 (d, 3H); 1.40 (m, 2H); 1.52 (m, 2H); 4.20 (m, 1H); 6.89 (d,1H); 8.71 (d, 1H); 9.27 (d, br, 1H); 13.4 (br, 1H) 1525 [CDCl3] 0.88 (t,3H); 1.23 (d, 3H); 1.25-1.4 (m, 6H); 1.55 (m, 2H); 4.18 (m, 1H); 7.89(d, 1H); 8.70 (d, 1H); 9.28 (br, 1H); 13.2 (br, 1H) 1528 [CDCl3] 0.92(d, 6H); 1.22 (d, 3H), 1.35 (m, 1H); 1.50 (m, 1H); 1.68 (m, 1H); 4.28(m, 1H); 6.89 (d, 1H); 8.71 (d, 1H); 9.26 (d, br, 1H); 13.3 (br, 1H)1529 [CDCl3] 0.95 (s, 9H); 1.17 (d, 3H); 4.12 (m, 1H); 6.89 (d, 1H);8.73 (d, 1H); 9.30 (d, br, 1H), 12.8 (br, 1H) 1530 [CDCl3] 0.95 (dt,6H); 1.17 (d, 3H); 1.82 (m, 1H); 4.08 (m, 1H); 6.89 (d, 1H); 8.72 (d,1H); 9.31 (d, br, 1H); 13.2 (br, 1H) 1532 [CDCl3] 0.95 (t, 6H); 1.50 (m,2H); 1.66 (m, 2H); 4.00 (m, 1H); 6.89 (d, 1H); 8.72 (d, 1H); 9.21 (d,br, 1H); 13.3 (br, 1H) 1535 [DMSO] 3.32 (s, 6H); 3.45 (t, 2H); 4.50 (t,1H); 7.33 (d, br, 1H); 8.43 (d, 1H); 8.92 (br, 1H); 13.4 (br, 1H) 1537[DMSO] 3.38 (m, 2H); 3.52 (m, 2H); 4.80 (br, 1H); 7.37 (br, 1H); 8.45(d, 1H); 8.96 (br, 1H); 13.4 (br, 1H) 1538 [DMSO] 3.25 (s, 3H); 3.49 (m,4H); 7.37 (d, br, 1H); 8.44 (d, 1H); 8.97 (br, 1H); 13.5 (br, 1H) 1545[DMSO] 1.15 (d, 3H); 3.27 (s, 3H); 3.40 (m, 2H); 4.19 (m, 1H); 7.35 (d,br, 1H); 8.43 (d, 1H); 8.82 (br, 1H); 13.4 (br, 1H) 1547 [DMSO] 1.75 (m,2H); 3.25 (s, 3H); 3.40 (m, 4H); 7.38 (br, 1H); 8.40 (d, 1H); 8.94 (br,1H); 13.4 (br, 1H) 1595 [DMSO] 7.45 (d, 1H); 8.15 (br, 1H); 8.40 (br,1H); 8.50 (d, 1H); 13.7 (br, 1H) 1596 [DMSO] 2.82 (d, 3H); 7.42 (d, 1H);8.41 (d, 1H); 8.80 (br, 1H); 13.4 (br, 1H) 1597 [DMSO] 1.12 (t, 3H);3.31 (m, 2H); 7.41 (d, 1H); 8.41 (d, 1H); 8.85 (br, 1H); 13.45 (br, 1H)1598 [DMSO] 0.90 (t, 3H); 1.54 (m, 2H); 3.25 (q, 2H); 7.41 (d, 1H); 8.40(d, 1H); 8.85 (br, 1H); 13.45 (br) 1599 [DMSO] 1.17 (d, 6H); 4.10 (m,1H); 7.40 (d, 1H); 8.41 (d, 1H); 8.67 (d, br, 1H); 13.4 (br, 1H) 1600[DMSO] 0.57 (m, 2H); 0.75 (m, 2H); 2.86 (m, 1H); 7.41 (d, 1H); 8.37 (d,1H); 8.80 (br, 1H); 13.35 (br, 1H) 1601 [CDCl3] 0.95 (t, 3H); 1.40 (m,2H); 1.60 (m, 2H); 3.45 (q, 2H); 6.88 (d, 1H); 8.71 (d, 1H); 9.28 (br,1H); 12.9 (br, 1H) 1602 [CDCl3] 1.78 (m, 2H); 1.95 (m, 2H); 2.40 (m,2H); 4.57 (m, 1H); 6.86 (d, 1H); 8.70 (d, 1H); 9.45 (d, br, 1H); 12.9(br, 1H) 1603 [CDCl3] 1.45 (s, 9H); 6.85 (d, 1H); 8.67 (d, 1H); 9.15(br, 1H); 12.6 (br, 1H) 1604 [CDCl3] 3.05 (s, 6H); 7.07 (d, 1H); 7.80(d, 1H) 1609 [CDCl3] 1.22 (t, 6H); 3.40 (m, 4H); 7.02 (d, 1H); 7.72 (d,1H) 1617 [DMSO] 0.25 (m, 2H), 0.46 (m, 2H); 1.05 (m, 1H); 3.22 (m, 2H);7.45 (d, br, 1H); 8.45 (d, 1H); 8.95 (br, 1H); 13.4 (br, 1H) 1619 [DMSO]0.90 (s, 9H), 3.15 (d, 2H); 7.38 (d, br, 1H); 8.40 (d, 1H); 8.80 (br,1H); 13.4 (br, 1H) 1625 [DMSO] 0.90 (d, 6H); 1.82 (m, 1H); 3.14 (t, 2H);7.39 (d, 1H); 8.40 (d, 1H); 8.91 (t, br, 1H) 1627 [CDCl3] 0.92 (d, 6H);1.49 (m, 2H); 1.68 (m, 1H); 3.46 (m, 2H); 6.87 (d, 1H); 8.70 (d, 1H);9.22 (br, 1H); 12.8 (br, 1H) 1629 [DMSO] 3.95 (m, 2H); 5.15 (dd, 2H);5.90 (m, 1H); 7.40 (d, 1H); 8.40 (d, 1H); 8.95 (br, 1H); 13.4 (br, 1H)1633 [CDCl3] 1.78 (s, 3H); 4.02 (d, 2H); 4.88 (d, 2H); 6.87 (d 1H); 8.72(d, 1H); 9.42 (br, 1H); 12.7 (br, 1H) 1634 [CDCl3] 2.23 (m, 1H); 4.23(m, 2H); 6.88 (d, 1H); 8.73 (d, 1H); 9.51 (br, 1H), 12.8 (br, 1H) 1636[DMSO] 0.89 (t, 3H); 1.14 (d, 3H); 1.51 (m, 2H); 3.95 (m, 1H); 7.41 (d,1H); 8.40 (d, 1H); 8.60 (br, 1H); 13.6 (br, 1H) 1638 [DMSO] 0.87 (t,3H); 1.15 (d, 3H); 1.32 (m, 2H); 1.46 (m, 2H); 4.03 (m, 1H); 7.40 (d,1H); 8.40 (d, 1H); 8.51 (br, 1H); 13.4 (br, 1H) 1639 [CDCl3] 0.88 (t,3H); 1.21 (d, 3H); 1.32 (m, 6H); 1.50 (m, 2H); 4.18 (m, 1H); 6.88 (d,1H); 8.71 (d, 1H); 9.12 (d, br, 1H), 12.9 (br, 1H) 1642 [CDCl3] 0.92 (t,6H); 1.20 (d, 3H); 1.32 (m, 1H); 1.46 (m, 1H); 1.67 (m, 1H); 4.27 (m,1H); 6.88 (d, 1H); 8.71 (d, 1H); 9.12 (d, br, 1H), 12.9 (br, 1H) 1643[CDCl3] 0.93 (s, 9H); 1.15 (d, 3H); 4.12 (m, 1H); 6.88 (d, 1H); 8.72 (d,1H); 9.22 (d, br, 1H) 1644 [CDCl3] 0.95 (m, 6H); 1.15 (d, 3H); 1.78 (m,1H); 4.05 (m, 1H); 6.88 (d, 1H); 8.72 (d, 1H); 9.18 (d, br, 1H); 12.7(br, 1H) 1646 [DMSO] 0.87 (t, 6H); 1.45 (m, 2H); 1.55 (m, 2H); 3.81 (m,1H); 7.40 (d, 1H); 8.40 (d, 1H); 8.52 (d, br, 1H); 13.4 (br, 1H) 1649[CDCl3] 3.40 (s, 6H); 3.61 (t, 2H); 4.50 (t, 1H); 6.87 (d, 1H); 8.69 (d,1H); 9.32 (br, 1H); 12.3 (br, 1H) 1651 [CDCl3] 3.63 (m, 2H); 3.84 (m,2H); 6.88 (d, 1H); 8.68 (d, 1H); 9.60 (br, 1H) 1652 [DMSO] 3.25 (s, 3H);3.50 (m, 4H); 7.40 (d, br, 1H); 8.45 (d, 1H); 8.92 (br, 1H); 13.5 (br,1H) 1659 [DMSO] 1.15 (d, 3H); 3.25 (s, 3H); 3.38 (m, 2H); 4.17 (m, 1H);7.40 (d, br, 1H); 8.43 (d, 1H); 8.75 (br, 1H); 13.5 (br, 1H) 1661 [DMSO]1.74 (m, 2H); 3.22 (s, 3H); 3.37 (m, 4H); 7.42 (d, br, 1H); 8.42 (d,1H); 8.90 (br, 1H); 13.4 (br, 1H) 1666 [CDCl3] 3.77 (s, 3H); 4.23 (d,2H); 6.87 (d, 1H); 8.67 (d, 1H); 9.65 (br, 1H); 12.1 (br, 1H) 1711[DMSO] 2.83 (d, 3H); 8.39 (s, 1H); 8.72 (d, br, 1H); 13.5 (br) 1712[DMSO] 1.11 (t, 3H); 3.30 (m, 2H); 8.40 (s, 1H); 8.75 (t, br, 1H) 1713[CDCl3] 0.99 (t, 3H); 1.62 (m, 2H); 3.41 (q, 2H); 8.56 (s, 1H); 9.00(br, 1H) 1714 [CDCl3] 1.24 (d, 6H); 4.22 (m, 1H); 8.41 (s, 1H); 9.17(br, 1H) 1715 [CDCl3] 0.61 (m, 2H); 0.90 (m, 2H); 2.95 (m, 1H); 8.57 (s,1H); 9.02 (br, 1H) 1716 [CDCl3] 0.94 (t, 3H); 1.41 (m, 2H); 1.58 (m,2H); 3.45 (m, 2H); 8.54 (s, 1H); 9.05 (br, 1H) 1717 [CDCl3] 1.80 (m,2H); 1.98 (m, 2H); 2.42 (m, 2H); 4.55 (m, 1H); 8.55 (s, 1H); 9.01 (br,1H); 12.0 (br, 1H) 1719 [DMSO] 2.83 (s, 3H); 2.97 (s, 3H); 8.04 (s, 1H);12.6 (br, 1H) 1720 [DMSO] 1.03 (t, 3H); 1.15 (t, 3H); 3.12 (q, 2H); 3.45(q, 2H); 8.05 (s, 1H); 12.5 (br, 1H) 1721 [CDCl3] 0.25 (m, 2H); 0.55 (m,2H); 1.05 (m, 1H); 3.32 (m, 2H); 8.57 (s, 1H); 8.93 (br, 1H); 12.1 (br,1H) 1722 [CDCl3] 0.96 (s, 9H); 3.28 (d, 2H); 8.59 (s, 1H); 9.05 (br, 1H)1723 [CDCl3] 0.95 (d, 6H); 1.90 (m, 1H); 3.29 (t, 2H); 8.59 (s, 1H);9.00 (br, 1H); 12.0 (br, 1H) 1725 [CDCl3] 0.94 (d, 6H); 1.49 (q, 2H);1.65 (m, 1H); 3.45 (m, 2H); 8.59 (s, 1H); 8.93 (br, 1H); 12.1 (br, 1H)1727 [CDCl3] 4.08 (m, 2H); 5.21 (dd, 2H); 5.90 (m, 1H); 8.60 (s, 1H);9.05 (br, 1H); 12.1 (br, 1H) 1728 [CDCl3] 1.78 (s, 3H); 4.01 (d, 2H);4.90 (d, 2H); 8.61 (s, 1H); 9.09 (br, 1H); 11.9 (br, 1H) 1729 [CDCl3]2.25 (m, 1H); 4.23 (m, 2H); 8.63 (s, 1H); 9.23 (br, 1H); 11.9 (br, 1H)1731 [CDCl3] 0.95 (t, 3H); 1.23 (d, 3H); 1.58 (m, 2H); 4.11 (m, 1H);8.55 (s, 1H); 8.60 (br, 1H) 1733 [CDCl3] 0.92 (t, 3H); 1.23 (d, 3H);1.39 (m, 2H); 1.52 (m, 2H); 4.20 (m, 1H); 8.55 (s, 1H); 8.66 (br, 1H)1734 [CDCl3] 0.87 (t, 3H); 1.22 (d, 3H); 1.35 (m, 6H); 1.52 (m, 2H);4.17 (m, 1H); 8.52 (s, 1H); 8.61 (br, 1H) 1735 [CDCl3] 0.94 (m, 6H);1.23 (d, 3H); 1.33 (m, 1H); 1.45 (m, 1H); 1.65 (m, 1H); 4.27 (m, 1H);8.56 (s, 1H); 8.63 (br, 1H); 11.9 (br) 1736 [CDCl3] 0.96 (s, 9H); 1.17(d, 3H); 4.08 (m, 1H); 8.57 (s, 1H); 8.80 (d, br, 1H) 1737 [CDCl3] 0.95(m, 6H); 1.18 (d, 3H); 1.80 (m, 1H); 4.05 (m, 1H); 8.57 (s, 1H); 8.73(d, br, 1H) 1738 [DMSO] 0.87 (t, 6H), 1.45 (m, 2H), 1.55 (m, 2H); 3.80(m, 1H); 8.40 (s, 1H); 8.42 (d, br, 1H); 13.4 (br, 1H) 1739 [CDCl3] 3.42(s, 6H); 3.63 (t, 2H); 4.50 (t, 1H); 8.49 (s, 1H); 8.74 (br, 1H); 11.4(br, 1H) 1741 [CDCl3] 3.65 (m, 2H); 3.85 (m, 2H); 8.55 (s, 1H); 9.16(br, 1H) 1742 [CDCl3] 3.40 (s, 3H); 3.57 (m, 2H); 3.67 (m, 2H); 8.47 (s,1H); 8.75 (br, 1H); 11.5 (br, 1H) 1744 [CDCl3] 1.27 (d, 3H); 3.39 (s,3H); 3.45 (m, 2H); 4.37 (m, 1H); 8.45 (s, 1H); 8.57 (br, 1H); 11.6 (br,1H) 1745 [CDCl3] 1.90 (m, 2H); 3.40 (s, 3H); 3.56 (m, 4H); 8.27 (s, 1H);8.65 (br, 1H); 11.8 (br, 1H) 1746 [DMSO] 3.67 (s, 3H); 4.13 (d, 2H);8.38 (s, 1H); 9.12 (br, 1H); 13.6 (br, 1H) 1751 [DMSO] 8.24 (br, 1H);8.38 (br, 1H); 8.61 (br, 1H); 13.7 (br, 1H) 1752 [CDCl3] 3.00 (d, 3H);8.71 (s, 1H); 8.91 (br, 1H); 12.2 (br, 1H) 1753 [CDCl3] 1.23 (t, 3H);3.49 (m, 2H); 8.71 (s, 1H); 8.89 (br, 1H); 12.1 (br, 1H) 1754 [CDCl3]0.98 (t, 3H); 1.62 (m, 2H); 3.40 (q, 2H); 8.70 (s, 1H); 8.90 (br, 1H)1755 [CDCl3] 1.25 (d, 6H); 4.25 (m, 1H); 8.68 (br, 2H); 12.0 (br, 1H)1756 [CDCl3] 0.61 (m, 2H); 0.89 (m, 2H); 2.95 (m, 1H); 8.70 (s, 1H);8.97 (br, 1H) 1757 [CDCl3] 0.94 (t, 3H); 1.40 (m, 2H); 1.58 (m, 2H);3.45 (m, 2H); 8.69 (s, 1H); 8.88 (br, 1H); 12.0 (br, 1H) 1758 [CDCl3]1.80 (m, 2H); 1.98 (m, 2H); 2.41 (m, 2H); 4.55 (m, 1H); 8.67 (s, 1H);8.98 (br, 1H); 12.1 (br, 1H) 1759 [CDCl3] 1.32 (s, 9H); 8.50 (br, 1H);8.60 (s, 1H) 1760 [CDCl3] 3.12 (s, 6H); 7.99 (s, 1H) 1761 [CDCl3] 1.24(t, 6H); 3.43 (m, 4H); 7.89 (s, 1H) 1762 [CDCl3] 0.28 (m, 2H); 0.55 (m,2H); 1.03 (m, 1H); 3.31 (m, 2H); 8.67 (s, 1H); 8.85 (br, 1H); 11.9 (br,1H) 1763 [CDCl3] 0.96 (s, 9H); 3.27 (d, 2H); 8.71 (s, 1H); 9.00 (br, 1H)1764 [CDCl3] 0.95 (d, 6H); 1.89 (m, 1H); 3.28 (t, 2H); 8.70 (s, 1H);8.97 (br, 1H) 1766 [CDCl3] 0.95 (d, 6H); 1.48 (q, 2H); 1.65 (m, 1H);3.45 (m, 2H); 8.69 (s, 1H); 8.85 (br, 1H); 12.0 (br, 1H) 1768 [CDCl3]4.08 (m, 2H); 5.21 (dd, 2H); 5.89 (m, 1H); 8.71 (s, 1H); 9.02 (br, 1H);12.1 (br, 1H) 1769 [CDCl3] 1.77 (s, 3H); 4.01 (d, 2H); 4.87 (d, 2H);8.71 (s, 1H); 9.03 (br, 1H) 1770 [CDCl3] 2.23 (m, 1H); 4.23 (m, 2H);8.72 (s, 1H); 9.20 (br, 1H); 12.0 (br, 1H) 1772 [CDCl3] 0.95 (t, 3H);1.21 (d, 3H); 1.55 (m, 2H); 4.10 (m, 1H); 8.67 (br, 1H); 8.70 (s, 1H);12.1 (br, 1H) 1774 [CDCl3] 0.91 (t, 3H); 1.21 (d, 3H); 1.38 (m, 2H);1.50 (m, 2H); 4.19 (m, 1H); 8.64 (br, 1H); 8.69 (s, 1H); 12.0 (br, 1H)1775 [CDCl3] 0.89 (t, 3H); 1.21 (d, 3H); 1.33 (m, 6H); 1.51 (m, 2H);4.17 (m, 1H); 8.60 (br, 1H); 8.68 (s, 1H) 1776 [CDCl3] 0.90 (m, 6H);1.21 (d, 3H); 1.31 (m, 1H); 1.45 (m, 1H); 1.64 (m, 1H); 4.25 (m, 1H);8.60 (br, 1H); 8.69 (s, 1H) 1777 [CDCl3] 0.94 (s, 9H); 1.15 (d, 3H);4.08 (m, 1H); 8.69 (s, 1H); 8.79 (br, 1H) 1778 [CDCl3] 0.93 (m, 6H);1.17 (d, 3H); 1.79 (m, 1H); 4.05 (m, 1H); 8.67 (s, 1H); 8.71 (br, 1H)1780 [CDCl3] 0.92 (t, 6H); 1.48 (m, 2H); 1.62 (m, 2H); 3.96 (m, 1H);8.61 (s, 1H); 9.16 (d, br, 1H) 1781 [CDCl3] 3.40 (s, 6H); 3.61 (t, 2H);4.50 (t, 1H); 8.63 (s, 1H); 8.76 (br, 1H) 1783 [CDCl3] 3.64 (m, 2H);3.86 (m, 2H); 8.68 (s, 1H); 9.17 (br, 1H) 1784 [CDCl3] 3.49 (s, 3H);3.55 (m, 2H); 3.66 (m, 2H); 8.62 (s, 1H); 8.77 (br, 1H) 1785 [CDCl3]1.27 (d, 3H); 3.39 (s, 3H); 3.44 (m, 2H); 4.37 (m, 1H); 8.56 (br, 1H);8.60 (s, 1H); 11.9 (br, 1H) 1786 [CDCl3] 1.90 (m, 2H); 3.40 (s, 3H);3.58 (m, 4H); 8.40 (s, 1H); 8.65 (br, 1H) 1787 [CDCl3] 3.78 (s, 3H);4.24 (d, 2H); 8.69 (s, 1H); 9.25 (br, 1H); 11.5 (br, 1H) 1792 [DMSO]8.22 (br, 1H); 8.37 (br, 1H); 8.81 (br, 1H); 13.7 (br, 1H) 1793 [CDCl3]3.00 (d, 3H); 8.80 (s, br, 2H); 12.0 (br, 1H) 1794 [CDCl3] 1.24 (t, 3H);3.49 (m, 2H); 8.40 (s, br, 2H); 12.0 (br, 1H) 1795 [DMSO] 0.89 (t, 3H);1.53 (m, 2H); 3.26 (q, 2H); 8.72 (s, 1H); 8.78 (t, br, 1H); 13.4 (br,1H) 1796 [DMSO] 1.18 (d, 6H); 4.08 (m, 1H); 8.60 (d, br, 2H); 13.4 (br,1H) 1797 [DMSO] 0.60 (m, 2H); 0.75 (m, 2H); 2.88 (m, 1H); 8.68 (s, 1H);8.77 (d, br, 1H); 13.3 (br, 1H) 1798 [CDCl3] 0.94 (t, 3H); 1.40 (m, 2H);1.59 (m, 2H); 3.44 (m, 2H); 8.79 (s, br, 2H) 1799 [DMSO] 1.70 (m, 2H);2.05 (m, 2H); 2.27 (m, 2H); 4.39 (m, 1H); 8.71 (s, 1H); 8.95 (d, br,1H); 13.4 (br, 1H) 1800 [CDCl3] 1.43 (s, 9H); 8.70 (br, 1H); 8.85 (s,1H); 11.5 (br) 1801 [CDCl3] 3.10 (s, 6H); 8.20 (s, 1H) 1802 [CDCl3] 1.23(t, 6H); 3.43 (m, br, 4H); 8.12 (s, 1H) 1803 [DMSO] 0.26 (m, 2H); 0.50(m, 2H); 1.05 (m, 1H); 3.19 (t, 2H); 8.76 (s, 1H); 8.87 (br, 1H); 13.5(br, 1H) 1804 [DMSO] 0.91 (s, 9H); 3.13 (d, 2H); 8.61 (t, br, 1H); 8.68(s, 1H); 13.4 (br, 1H) 1805 [DMSO] 0.89 (d, 6H); 1.84 (m, 1H); 3.14 (t,2H); 8.70 (s, 1H); 8.75 (t, br, 1H); 13.4 (br, 1H) 1807 [DMSO] 0.89 (d,6H); 1.40 (q, 2H); 1.62 (m, 1H); 3.30 (m, 2H); 8.71 (s, 1H); 8.73 (t,br, 1H); 13.4 (br, 1H) 1809 [DMSO] 3.93 (m, 2H); 5.18 (dd, 2H); 5.90 (m,1H); 8.71 (s, 1H); 8.89 (t, br, 1H); 13.4 (br, 1H) 1810 [DMSO] 1.72 (s,3H); 3.87 (d, 2H); 4.85 (d, 2H); 8.71 (s, 1H); 8.87 (t, br, 1H); 13.3(br, 1H) 1811 [DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.69 (s, 1H); 9.01 (t,br, 1H); 13.4 (br, 1H) 1813 [DMSO] 0.87 (t, 3H); 1.14 (d, 3H); 1.50 (m,2H); 3.90 (m, 1H); 8.52 (d, br, 1H); 8.72 (s, 1H); 13.4 (br, 1H) 1815[DMSO] 0.89 (t, 3H); 1.15 (d, 3H); 1.30 (m, 2H); 1.47 (m, 2H); 4.00 (m,1H); 8.54 (br, 1H); 8.72 (s, 1H); 13.4 (br, 1H) 1816 [CDCl3] 0.89 (t,3H); 1.20 (d, 3H); 1.27-1.37 (m, 6H); 1.51 (m, 2H); 4.16 (m, 1H); 8.75(br, 1H); 8.90 (s, 1H); 12.1 (br, 1H) 1817 [CDCl3] 0.91 (m, 6H); 1.20(d, 3H); 1.32 (m, 1H); 1.45 (m, 1H); 1.65 (m, 1H); 4.25 (m, 1H); 8.66(br, 1H); 8.90 (s, 1H); 11.9 (br, 1H) 1818 [CDCl3] 0.94 (s, 9H); 1.14(d, 3H); 4.07 (m, 1H); 8.85 (br, 1H); 8.90 (s, 1H) 1819 [CDCl3] 0.95 (m,6H); 1.18 (d, 3H); 1.79 (m, 1H); 4.04 (m, 1H); 8.75 (br, 1H); 8.89 (s,1H) 1820 [CDCl3] 0.93 (t, 6H); 1.48 (m, 2H); 1.64 (m, 2H); 3.98 (m, 1H);8.63 (br, 1H); 8.90 (s, 1H); 11.6 (br, 1H) 1821 [CDCl3] 3.40 (s, 6H);3.60 (t, 2H); 4.49 (t, 1H); 8.85 (s, br, 2H); 11.4 (br, 1H) 1823 [CDCl3]3.63 (m, 2H); 3.83 (m, 2H); 8.86 (s, 1H); 9.17 (br, 1H) 1824 [CDCl3]3.38 (s, 3H); 3.55 (m, 2H); 3.65 (m, 2H); 8.82 (s, 1H); 8.84 (br, 1H);11.4 (br, 1H) 1826 [CDCl3] 1.25 (d, 3H); 3.39 (s, 3H); 3.43 (m, 2H);4.38 (m, 1H); 8.67 (br, 1H); 8.82 (s, 1H); 11.5 (br, 1H) 1827 [CDCl3]1.89 (m, 2H); 3.40 (s, 3H); 3.55 (m, 4H); 8.67 (s, 1H); 8.74 (br, 1H);11.8 (br, 1H) 1828 [CDCl3] 3.78 (s, 3H); 4.24 (d, 2H); 8.89 (s, 1H);9.30 (br, 1H) 1833 [DMSO] 2.85 (d, 3H); 8.69 (s, 1H); 8.71 (br, 1H);13.5 (br, 1H) 1834 [DMSO] 1.12 (t, 3H); 3.30 (m, 2H); 8.70 (s, 1H); 8.75(t, br, 1H); 13.5 (br, 1H) 1835 [DMSO] 0.89 (t, 3H); 1.52 (m, 2H); 3.25(q, 2H); 8.70 (s, 1H); 8.75 (t, br, 1H); 13.5 (br, 1H) 1837 [DMSO] 0.59(m, 2H); 0.76 (m, 2H); 2.86 (m, 1H); 8.66 (s, 1H); 8.76 (br, 1H); 13.3(br) 1838 [CDCl3] 0.95 (t, 3H); 1.42 (m, 2H); 1.60 (m, 2H); 3.45 (m,2H); 8.86 (s, 1H); 8.95 (br, 1H) 1839 [CDCl3] 1.81 (m, 2H); 2.00 (m,2H); 2.42 (m, 2H); 4.54 (m, 1H); 8.84 (s, 1H); 9.17 (d, br, 1H); 12.2(br, 1H) 1845 [CDCl3] 0.29 (m, 2H); 0.57 (m, 2H); 1.05 (m, 1H); 3.32 (t,2H); 8.87 (s, 1H); 9.05 (br, 1H); 12.3 (br, 1H) 1847 [CDCl3] 1.00 (d,6H); 1.90 (m, 1H); 3.30 (t, 2H); 8.85 (s, 1H); 9.00 (br, 1H) 1849[CDCl3] 0.95 (d, 6H); 1.51 (q, 2H); 1.68 (m, 1H); 3.46 (m, 2H); 8.85 (s,1H); 8.91 (br, 1H) 1851 [DMSO] 3.94 (m, 2H); 5.16 (dd, 2H); 5.90 (m,1H); 8.70 (s, 1H); 8.85 (t, br, 1H); 13.4 (br, 1H) 1852 [CDCl3] 1.79 (s,3H); 4.02 (m, 2H); 4.92 (m, 2H); 8.88 (s, 1H); 9.10 (t, br, 1H) 1853[CDCl3] 2.26 (m, 1H); 4.22 (m, 2H); 8.86 (s, 1H); 9.25 (br, 1H) 1854[DMSO] 0.87 (t, 3H); 1.13 (d, 3H); 1.50 (m, 2H); 3.91 (m, 1H); 8.55 (d,br, 1H); 8.70 (br, 1H); 13.5 (br, 1H) 1856 [DMSO] 0.89 (t, 3H); 1.15 (d,3H); 1.30 (m, 2H); 1.49 (m, 2H); 4.01 (m, 1H); 8.51 (d, br, 1H); 8.71(s, 1H); 13.6 (br, 1H) 1857 [CDCl3] 0.87 (t, 3H); 1.22 (d, 3H);1.25-1.35 (m, 6H); 1.53 (m, 2H); 4.14 (m, 1H); 8.81 (d, br, 1H); 8.88(s, 1H) 1858 [CDCl3] 0.92 (m, 6H); 1.22 (d, 3H); 1.33 (m, 1H); 1.48 (m,1H); 1.65 (m, 1H); 4.25 (m, 1H); 8.84 (br, 1H); 8.88 (s, 1H); 12.3 (br,1H) 1860 [CDCl3] 0.95 (m, 6H); 1.18 (d, 3H); 1.81 (m, 1H); 4.05 (m, 1H);8.90 (s, 1H); 9.01 (d, br, 1H) 1861 [DMSO] 0.88 (t, 6H); 1.45 (m, 2H);1.55 (m, 2H); 3.79 (m, 1H); 8.40 (d, br, 1H); 8.70 (s, 1H); 13.5 (br,1H) 1867 [DMSO] 3.29 (s, 3H); 3.47 (m, 4H); 8.73 (s, 1H); 8.79 (br, 1H);13.6 (br, 1H) 1869 [CDCl3] 1.28 (d, 3H); 3.39 (s, 3H); 3.45 (m, 2H);4.35 (m, 1H); 8.81 (s, 1H); 8.86 (br, 1H); 12.0 (br, 1H) 1870 [CDCl3]1.90 (m, 2H); 3.41 (s, 3H); 3.56 (m, 4H); 8.62 (s, 1H); 8.76 (br, 1H);11.9 (br, 1H) 1876 [DMSO] 8.18 (br, 1H); 8.35 (br, 1H); 8.79 (s, 1H);13.7 (br, 1H) 1877 [DMSO] 2.83 (d, 3H); 8.70 (br, 2H); 13.5 (br, 1H)1878 [DMSO] 1.12 (t, 3H); 3.32 (m, 2H); 8.71 (s, 1H); 8.76 (t, br, 1H);13.4 (br, 1H) 1879 [DMSO] 0.90 (t, 3H); 1.51 (m, 2H); 3.25 (q, 2H); 8.70(s, 1H); 8.78 (t, br, 1H); 13.5 (br, 1H) 1880 [DMSO] 1.18 (d, 6H); 4.07(m, 2H); 8.57 (d, br, 1H); 8.72 (s, 1H); 13.4 (br, 1H) 1881 [DMSO] 0.58(m, 2H); 0.74 (m, 2H); 2.85 (m, 1H); 8.66 (s, 1H); 8.74 (br, 1H); 13.4(br, 1H) 1882 [DMSO] 0.89 (t, 3H); 1.31 (m, 2H); 1.50 (m, 2H); 3.30 (m,2H); 8.70 (s, 1H); 8.75 (br, 1H) 1883 [DMSO] 1.69 (m, 2H); 2.02 (m, 2H);2.25 (m, 2H); 4.39 (m, 1H); 8.70 (s, 1H); 8.95 (br, 1H) 1884 [CDCl3]1.47 (s, 9H); 8.87 (s, 1H); 9.02 (br, 1H); 12.2 (br, 1H) 1885 [CDCl3]3.12 (s, 6H); 8.16 (s, 1H) 1886 [DMSO] 0.23 (m, 2H); 0.45 (m, 2H); 1.02(m, 1H); 3.19 (t, 2H); 8.72 (s, 1H); 8.83 (br, 1H); 13.4 (br, 1H) 1887[DMSO] 0.90 (s, 9H); 3.14 (d, 2H); 8.72 (br, 1H); 8.67 (s, 1H); 13.4(br, 1H) 1888 [DMSO] 0.90 (d, 6H); 1.84 (m, 1H); 3.12 (t, 2H); 8.68 (s,1H); 8.73 (t, br, 1H); 13.4 (br, 1H) 1890 [DMSO] 0.90 (d, 6H); 1.41 (m,2H); 1.60 (m, 1H); 3.30 (m, 2H); 8.69 (s, 1H); 8.72 (t, br, 1H); 13.5(br, 1H) 1892 [DMSO] 3.94 (m, 2H); 5.15 (dd, 2H); 5.89 (m, 1H); 8.70 (s,1H); 8.85 (t, br, 1H) 1894 [DMSO] 1.70 (s, 3H); 3.86 (d, 2H); 4.84 (d,2H); 8.68 (s, 1H); 8.95 (br, 1H); 13.4 (br, 1H) 1895 [DMSO] 3.10 (t,1H); 4.05 (m, 2H); 8.25 (br, 1H); 8.30 (s, 1H); 11.5 (br, 1H) 1897[CDCl3] 0.95 (t, 3H); 1.24 (d, 3H); 1.60 (m, 2H); 4.10 (m, 1H); 8.87(br, 2H) 1899 [CDCl3] 0.92 (t, 3H); 1.23 (d, 3H); 1.40 (m, 2H); 1.52 (m,2H); 4.17 (m, 1H); 8.88 (s, 1H); 8.91 (br, 1H) 1900 [DMSO] 0.86 (t, 3H);1.15 (d, 3H); 1.25 (m, 6H); 1.48 (m, 2H); 4.00 (m, 1H); 8.53 (d, br,1H); 8.71 (s, 1H); 13.4 (br, 1H) 1903 [DMSO] 0.89 (d, 6H); 1.13 (d, 3H);1.27 (m, 1H); 1.48 (m, 1H); 1.62 (m, 1H); 4.09 (m, 1H); 8.50 (d, br,1H); 8.71 (s, 1H); 13.5 (br, 1H) 1904 [DMSO] 0.81 (s, 9H); 1.07 (d, 3H);3.90 (m, 1H); 8.43 (d, br, 1H); 8.67 (s, 1H); 13.4 (br, 1H) 1905 [DMSO]0.88 (d, 6H); 1.10 (d, 3H); 1.75 (m, 1H); 1.48 (m, 1H); 3.85 (m, 1H);8.49 (d, br, 1H); 8.70 (s, 1H); 13.5 (br, 1H) 1907 [DMSO] 0.87 (t, 6H);1.43 (m, 2H); 1.55 (m, 2H); 3.78 (m, 1H); 8.55 (br, 1H); 8.67 (s, 1H);13.5 (br, 1H) 1910 [CDCl3] 3.41 (s, 6H); 3.62 (t, 2H); 4.50 (t, 1H);8.82 (s, 1H); 8.95 (br, 1H); 11.2 (br, 1H) 1912 [DMSO] 3.39 (m, 2H);3.52 (m, 2H); 4.83 (br, 1H); 8.76 (s, 1H); 8.80 (t, br, 1H); 13.6 (br,1H) 1913 [DMSO] 3.26 (s, 3H); 3.47 (m, 4H); 8.71 (s, 1H); 8.79 (br, 1H)1916 [CDCl3] 1.27 (d, 3H); 3.39 (s, 3H); 3.44 (m, 2H); 4.38 (m, 1H);8.83 (s, 1H); 8.95 (br, 1H); 12.1 (br, 1H) 1917 [DMSO] 1.75 (m, 2H);3.24 (s, 3H); 3.39 (m, 4H); 8.70 (s, 1H); 8.81 (br, 1H); 13.4 (br, 1H)1918 [DMSO] 3.66 (s, 3H); 4.12 (d, 2H); 8.71 (s, 1H); 9.02 (t, br, 1H),13.5 (br, 1H) 1923 [DMSO] 2.81 (d, 3H); 8.72 (s, 1H); 8.77 (br, 1H);13.4 (br) 1924 [DMSO] 1.14 (t, 3H); 3.35 (m, 2H); 8.74 (s, 1H); 8.82 (t,br, 1H); 13.4 (br) 1925 [DMSO] 0.89 (t, 3H); 1.53 (m, 2H); 3.28 (q, 2H);8.73 (s, 1H); 8.80 (t, br, 1H) 1926 [DMSO] 1.18 (d, 6H); 4.10 (m, 1H);8.63 (d, br, 1H); 8.75 (s, 1H); 13.4 (br, 1H) 1927 [DMSO] 0.60 (m, 2H);0.75 (m, 2H); 2.87 (m, 1H); 8.69 (s, 1H); 8.80 (br, 1H) 1928 [DMSO] 0.89(t, 3H); 1.34 (m, 2H); 1.51 (m, 2H); 3.30 (m, 2H); 8.72 (s, 1H); 8.79(br, 1H) 1929 [DMSO] 1.72 (m, 2H); 2.05 (m, 2H); 2.27 (m, 2H); 4.38 (m,1H); 8.73 (s, 1H); 9.00 (d, br, 1H); 13.3 (br) 1930 [DMSO] 1.37 (s, 9H);8.30 (br, 1H); 8.66 (s, 1H); 13.4 (br) 1931 [DMSO] 2.80 (s, 3H); 2.96(s, 3H); 8.27 (s, 1H); 12.4 (br, 1H) 1932 [DMSO] 1.01 (t, 3H); 1.11 (t,3H); 3.10 (q, 2H); 3.42 (q, 2H); 8.25 (s, 1H); 12.3 (br, 1H) 1933 [DMSO]0.26 (m, 2H); 0.47 (m, 2H); 1.04 (m, 1H); 3.20 (m, 2H); 8.77 (s, 1H);8.87 (t, br, 1H); 13.5 (br, 1H) 1934 [DMSO] 0.90 (s, 9H); 3.13 (d, 2H);8.62 (t, br, 1H); 8.70 (s, 1H); 13.3 (br, 1H) 1935 [DMSO] 0.90 (d, 6H);1.85 (m, 1H); 3.13 (m, 2H); 8.71 (s, 1H); 8.75 (t, br, 1H); 13.4 (br,1H) 1937 [CDCl3] 0.94 (d, 6H); 1.49 (q, 2H); 1.66 (m, 1H); 3.46 (m, 2H);8.75 (br, 1H); 8.85 (s, 1H); 11.5 (br) 1939 [DMSO] 3.93 (m, 2H); 5.19(dd, 2H); 5.89 (m, 1H); 8.72 (s, 1H); 8.90 (t, br, 1H); 13.3 (br, 1H)1941 [DMSO] 1.72 (s, 3H); 3.87 (d, 2H); 4.87 (d, 2H); 8.73 (s, 1H); 8.89(t, br, 1H); 13.3 (br) 1942 [DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.70 (s,1H); 9.04 (t, br, 1H); 13.3 (br, 1H) 1944 [DMSO] 0.89 (t, 3H); 1.14 (d,3H); 1.51 (m, 2H); 3.91 (m, 1H); 8.55 (d, br, 1H); 8.75 (s, 1H); 13.4(br, 1H) 1946 [DMSO] 0.89 (t, 3H); 1.15 (d, 3H); 1.31 (m, 2H); 1.47 (m,2H); 4.01 (m, 1H); 8.56 (br, 1H); 8.74 (s, 1H); 13.4 (br, 1H) 1947[DMSO] 0.85 (t, 3H); 1.15 (d, 3H); 1.20-1.35 (m, 6H); 1.49 (m, 2H); 4.00(m, 1H); 8.58 (d, br, 1H); 8.74 (s, 1H); 13.4 (br, 1H) 1948 [DMSO] 0.88(d, 6H); 1.15 (d, 3H); 1.27 (m, 1H); 1.48 (m, 1H); 1.61 (m, 1H); 4.10(m, 1H); 8.56 (d, br, 1H); 8.74 (s, 1H); 13.5 (br, 1H) 1949 [CDCl3] 0.94(s, 9H); 1.15 (d, 3H); 4.09 (m, 1H); 8.89 (br, 1H); 8.91 (s, 1H) 1950[CDCl3] 0.94 (m, 6H); 1.17 (d, 3H); 1.80 (m, 1H); 4.05 (m, 1H); 8.88(br, 1H); 8.92 (s, 1H) 1951 [CDCl3] 0.92 (t, 6H); 1.49 (m, 2H); 1.65 (m,2H); 3.99 (m, 1H); 8.78 (br, 1H); 8.92 (s, 1H) 1952 [CDCl3] 3.41 (s,6H); 3.61 (t, 2H); 4.50 (t, 1H); 8.84 (s, br, 2H); 11.4 (br, 1H) 1954[DMSO] 3.39 (m, 2H); 3.52 (m, 2H); 4.80 (br, 1H); 8.79 (s, 1H); 8.82 (t,br, 1H); 13.5 (br, 1H) 1955 [CDCl3] 3.38 (s, 3H); 3.55 (m, 2H); 3.66 (m,2H); 8.78 (s, br, 1H); 8.82 (s, 1H); 11.5 (br) 1957 [CDCl3] 1.27 (d,3H); 3.38 (s, 3H); 3.42 (m, 2H); 4.38 (m, 1H); 8.75 (br, 1H); 8.84 (s,1H); 12.3 (br, 1H) 1958 [CDCl3] 1.89 (m, 2H); 3.41 (s, 3H); 3.56 (m,4H); 8.61 (s, 1H); 8.68 (br, 1H); 11.8 (br, 1H) 1959 [DMSO] 3.67 (s,3H); 4.12 (d, 2H); 8.73 (s, 1H); 9.04 (t, br, 1H); 13.5 (br, 1H) 1964[DMSO] 8.25 (br, 1H); 8.37 (br, 1H); 8.47 (s, 1H); 13.7 (br, 1H) 1965[DMSO] 2.82 (d, 3H); 8.37 (s, 1H); 8.72 (d, br, 1H); 13.5 (br, 1H) 1966[DMSO] 1.13 (t, 3H); 3.34 (m, 2H); 8.39 (s, 1H); 8.76 (t, br, 1H); 13.5(br, 1H) 1967 [DMSO] 0.90 (t, 3H); 1.53 (m, 2H); 3.26 (q, 2H); 8.39 (s,1H); 8.75 (t, br, 1H); 13.5 (br, 1H) 1968 [DMSO] 1.18 (d, 6H); 4.09 (m,1H); 8.41 (s, 1H); 8.58 (d, br, 1H); 13.5 (br, 1H) 1969 [DMSO] 0.59 (m,2H); 0.75 (m, 2H); 2.86 (m, 1H); 8.34 (s, 1H); 8.73 (d, br, 1H); 13.4(br, 1H) 1970 [DMSO] 0.89 (t, 3H); 1.33 (m, 2H); 1.51 (m, 2H); 3.31 (m,2H); 8.39 (s, 1H); 8.73 (t, br, 1H); 13.5 (br, 1H) 1971 [DMSO] 1.70 (m,2H); 2.04 (m, 2H); 2.25 (m, 2H); 4.38 (m, 1H); 8.39 (s, 1H); 8.92 (d,br, 1H); 13.4 (br, 1H) 2006 [DMSO] 8.25 (br, 1H); 8.35 (br, 1H); 8.61(s, 1H); 13.7 (br, 1H) 2007 [DMSO] 2.82 (d, 3H); 8.51 (s, 1H); 8.74 (d,br, 1H); 13.5 (br, 1H) 2008 [DMSO] 1.13 (t, 3H); 3.33 (m, 2H); 8.53 (s,1H); 8.78 (t, br, 1H); 13.5 (br, 1H) 2009 [DMSO] 0.89 (t, 3H); 1.53 (m,2H); 3.26 (q, 2H); 8.51 (s, 1H); 8.76 (t, br, 1H); 13.5 (br, 1H) 2010[DMSO] 1.18 (d, 6H); 4.07 (m, 1H); 8.53 (s, 1H); 8.61 (d, br, 1H); 13.5(br, 1H) 2011 [DMSO] 0.58 (m, 2H); 0.74 (m, 2H); 2.86 (m, 1H); 8.48 (s,1H); 8.77 (d, br, 1H); 13.4 (br, 1H) 2012 [DMSO] 0.90 (t, 3H); 1.33 (m,2H); 1.51 (m, 2H); 3.30 (m, 2H); 8.52 (s, 1H); 8.77 (t, br, 1H); 13.5(br, 1H) 2013 [DMSO] 1.72 (m, 2H); 2.05 (m, 2H); 2.25 (m, 2H); 4.39 (m,1H); 8.51 (s, 1H); 8.95 (d, br, 1H); 13.4 (br, 1H) 2014 [DMSO] 1.37 (s,9H); 8.31 (br, 1H); 8.45 (s, 1H); 13.4 (br, 1H) 2015 [DMSO] 2.82 (s,3H); 2.95 (s, 3H); 8.12 (s, 1H); 12.5 (br, 1H) 2017 [DMSO] 0.26 (m, 2H);0.47 (m, 2H); 1.04 (m, 1H); 3.30 (m, 2H); 8.56 (s, 1H); 8.86 (t, br,1H); 13.5 (br, 1H) 2018 [DMSO] 0.91 (s, 9H); 3.13 (d, 2H); 8.47 (s, 1H);8.63 (t, br, 1H); 13.5 (br, 1H) 2019 [DMSO] 0.90 (d, 6H); 1.83 (m, 1H);3.13 (m, 2H); 8.50 (s, 1H); 8.73 (t, br, 1H); 13.4 (br, 1H) 2021 [DMSO]0.89 (d, 6H); 1.42 (q, 2H); 1.62 (m, 1H); 3.31 (m, 2H); 8.51 (s, 1H);8.75 (t, br, 1H); 13.5 (br, 1H) 2023 [DMSO] 3.94 (m, 2H); 5.18 (dd, 2H);5.89 (m, 1H); 8.52 (s, 1H); 8.88 (t, br, 1H); 13.4 (br, 1H) 2025 [DMSO]1.72 (s, 3H); 3.86 (d, 2H); 4.85 (d, 2H); 8.50 (s, 1H); 8.87 (t, br,1H); 13.4 (br, 1H) 2026 [DMSO] 3.18 (m, 1H); 4.10 (m, 2H); 8.48 (s, 1H);9.02 (t, br, 1H); 13.3 (br, 1H) 2030 [CDCl3] 0.93 (t, 3H); 1.23 (d, 3H);1.40 (m, 2H); 1.52 (m, 2H); 4.21 (m, 1H); 8.74 (s, 1H); 8.97 (d, br,1H); 12.9 (br, 1H) 2031 [DMSO] 0.85 (t, 3H); 1.15 (d, 3H); 1.20-1.35 (m,6H); 1.48 (m, 2H); 3.99 (m, 1H); 8.52 (s, 1H); 8.54 (d, br, 1H); 13.5(br, 1H) 2032 [DMSO] 0.88 (d, 6H); 1.14 (d, 3H); 1.27 (m, 1H); 1.48 (m,1H); 1.62 (m, 1H); 4.10 (m, 1H); 8.51 (s, 1H); 8.53 (d, br, 1H); 13.5(br, 1H) 2035 [DMSO] 0.86 (t, 6H); 1.45 (m, 2H); 1.55 (m, 2H); 3.78 (m,1H); 8.82 (d, br, 1H); 8.51 (s, 1H); 13.5 (br, 1H) 2036 [CDCl3] 3.41 (s,6H); 3.61 (t, 2H); 4.50 (t, 1H); 8.67 (s, 1H); 9.00 (br, 1H); 11.7 (br,1H) 2038 [DMSO] 3.35 (m, 2H); 3.53 (m, 2H); 4.81 (br, 1H); 8.56 (s, 1H);8.80 (t, br, 1H); 13.6 (br, 1H) 2039 [CDCl3] 3.38 (s, 3H); 3.56 (m, 2H);3.65 (m, 2H); 8.65 (s, 1H); 9.01 (s, 1H); 11.8 (br, 1H) 2041 [DMSO] 1.15(d, 3H); 3.30 (s, 3H); 3.40 (m, 2H); 4.18 (m, 1H); 8.52 (s, 1H); 8.64(d, br, 1H); 13.4 (br, 1H) 2048 [DMSO] 8.20 (br, 1H); 8.37 (br, 1H);8.81 (s, 1H); 13.7 (br, 1H) 2090 [DMSO] 7.45 (d, 1H); 8.14 (br, 1H);8.42 (br, 1H); 8.48 (d, 1H); 13.7 (br, 1H) 2091 [DMSO] 2.84 (d, 3H);7.42 (d, 1H); 8.41 (d, 1H); 8.79 (br, 1H); 13.4 (br, 1H) 2092 [DMSO]1.12 (t, 3H); 3.32 (m, 2H); 7.42 (d, 1H); 8.42 (d, 1H); 8.83 (br, 1H);13.4 (br, 1H) 2093 [DMSO] 0.89 (t, 3H); 1.54 (m, 2H); 3.27 (q, 2H); 7.42(d, 1H); 8.41 (d, 1H); 8.82 (br, 1H); 13.4 (br, 1H) 2094 [DMSO] 1.18 (d,6H); 4.11 (m, 1H); 7.41 (d, 1H); 8.41 (d, 1H); 8.63 (br, 1H); 13.4 (br,1H) 2095 [CDCl3] 0.61 (m, 2H); 0.88 (m, 2H); 3.00 (m, 1H); 6.89 (d, 1H);8.68 (d, 1H); 9.35 (br, 1H); 12.5 (br, 1H) 2096 [DMSO] 0.89 (t, 3H);1.33 (m, 2H); 1.52 (m, 2H); 3.32 (m, 2H); 7.42 (d, 1H); 8.41 (d, 1H);8.81 (br, 1H); 13.3 (br, 1H) 2097 [DMSO] 1.72 (m, 2H); 2.05 (m, 2H);2.46 (m, 2H); 4.41 (m, 1H); 7.43 (d, 1H); 8.39 (d, 1H); 8.96 (br, 1H);13.3 (br, 1H) 2101 [DMSO] 0.26 (m, 2H), 0.47 (m, 2H); 1.06 (m, 1H); 3.22(m, 2H); 7.45 (d, 1H); 8.45 (d, 1H); 8.91 (br, 1H); 13.4 (br, 1H) 2102[DMSO] 0.92 (s, 9H); 3.15 (d, 2H); 7.40 (d, 1H); 8.41 (d, 1H); 8.75 (br,1H); 13.3 (br, 1H) 2103 [DMSO] 0.90 (d, 6H); 1.83 (m, 1H); 3.14 (t, 2H);7.40 (d, 1H); 8.40 (d, 1H); 8.81 (t, br, 1H); 13.3 (br, 1H) 2105 [DMSO]0.90 (d, 6H); 1.42 (m, 2H); 1.62 (m, 1H); 3.33 (m, 2H); 7.41 (d, 1H);8.40 (d, 1H); 8.80 (br, 1H); 13.3 (br, 1H) 2107 [DMSO] 3.95 (t, 2H);5.17 (dd, 2H); 5.90 (m, 1H); 7.41 (d, 1H); 8.41 (d, 1H); 8.93 (br, 1H);13.3 (br, 1H) 2109 [DMSO] 1.72 (s, 3H); 3.88 (d, 2H); 4.85 (d, 2H); 7.42(d 1H); 8.42 (d, 1H); 8.94 (br, 1H); 13.3 (br, 1H) 2110 [DMSO] 3.17 (m,1H); 4.11 (m, 2H); 7.41 (d, 1H); 8.40 (d, 1H); 9.06 (br, 1H), 13.3 (br,1H) 2112 [DMSO] 0.89 (t, 3H); 1.15 (d, 3H); 1.53 (m, 2H); 3.95 (m, 1H);7.42 (d, 1H); 8.42 (d, 1H); 8.60 (br, 1H); 13.4 (br, 1H) 2114 [DMSO]0.88 (t, 3H); 1.15 (d, 3H); 1.32 (m, 2H); 1.48 (m, 2H); 4.04 (m, 1H);7.42 (d, 1H); 8.41 (d, 1H); 8.59 (br, 1H); 13.4 (br, 1H) 2115 [DMSO]0.85 (t, 3H); 1.16 (d, 3H); 1.20-1.35 (m, 6H); 1.50 (m, 2H); 4.02 (m,1H); 7.42 (d, 1H); 8.44 (d, 1H); 8.62 (d, br, 1H), 13.4 (br, 1H) 2116[DMSO] 0.88 (d, 6H); 1.14 (d, 3H); 1.25 (m, 1H); 1.48 (m, 1H); 1.63 (m,1H); 4.21 (m, 1H); 6.92 (d, 1H); 8.42 (d, 1H); 8.59 (d, br, 1H), 13.4(br, 1H) 2122 [DMSO] 3.40 (m, 2H); 3.52 (m, 2H); 4.82 (br, 1H); 7.44 (d,1H); 8.46 (d, 1H); 8.88 (br, 1H); 13.4 (br, 1H) 2133 [DMSO] 2.83 (d,3H); 8.58 (s, 1H); 8.82 (d, br, 1H); 13.4 (br, 1H) 2134 [DMSO] 1.14 (t,3H); 3.34 (m, 2H); 8.60 (s, 1H); 8.86 (t, br, 1H); 13.5 (br, 1H) 2135[DMSO] 0.89 (t, 3H); 1.54 (m, 2H); 3.26 (q, 2H); 8.59 (s, 1H); 8.85 (t,br, 1H); 13.5 (br, 1H) 2137 [DMSO] 0.60 (m, 2H); 0.75 (m, 2H); 2.88 (m,1H); 8.55 (s, 1H); 8.85 (d, br, 1H); 13.4 (br, 1H) 2138 [DMSO] 0.90 (t,3H); 1.33 (m, 2H); 1.51 (m, 2H); 3.31 (m, 2H); 8.59 (s, 1H); 8.84 (t,br, 1H); 13.4 (br, 1H) 2139 [DMSO] 1.71 (m, 2H); 2.05 (m, 2H); 2.25 (m,2H); 4.40 (m, 1H); 8.62 (s, 1H); 9.04 (d, br, 1H); 13.4 (br, 1H) 2143[DMSO] 0.26 (m, 2H); 0.47 (m, 2H); 1.05 (m, 1H); 3.20 (m, 2H); 8.63 (s,1H); 8.94 (t, br, 1H); 13.4 (br, 1H) 2144 [DMSO] 0.91 (s, 9H); 3.15 (d,2H); 8.55 (s, 1H); 8.66 (t, br, 1H); 13.3 (br, 1H)

3. Biological Examples 3.1 Scoring of the Damage

The damage to the plants is scored visually using a scale of 0-100%, incomparison to control plants:

0%=no noticeable effect compared to the untreated plant100%=the treated plants dies.

3.2 Post-Emergence Herbicide Action and Safener Action

Seeds or rhizome pieces of monocotyledonous and dicotyledonous harmfulplants and crop plants are placed in sandy loam soil in plastic pots,covered with soil and cultivated in the greenhouse under good growthconditions. Alternatively, harmful plants encountered in paddy ricecultivation are cultivated in pots in which the surface of the soil iscovered by up to 2 cm of water. Three weeks after sowing, the testplants are treated at the three-leaf stage. The herbicide/safener activecompound combinations according to the invention, formulated as emulsionconcentrates, and in parallel tests the individual active compoundsformulated in a corresponding manner, are sprayed at various dosages ata water application rate of 300 l/ha (converted) onto the green parts ofthe plants, and, after the test plants were left to stand in thegreenhouse for about 2 to 3 weeks under optimum growth conditions, theeffect of the preparations is scored visually in comparison to untreatedcontrols. In the case of rice or harmful plants encountered in thecultivation of rice, the active compounds are also added directly to theirrigation water (application analogously to the so-called granuleapplication) or sprayed onto the plants and into the irrigation water.

The tests show that the safeners according to the invention incombination with herbicides, in a herbicides:safener ratio of from 2:1to 1:20, considerably reduce the damage caused by the herbicide to cropplants such as corn, rice, wheat or barley or other cereals ordicotyledonous crop plants such as soybeans or oilseed rape compared tothe application of the individual herbicides without safener, such thatfrom 30% up to 100% less damage to the crop plant is observed. At thesame time, the action of the herbicide against economically importantharmful plants is not, or not essentially, adversely affected, so thatgood herbicidal post-emergence action against a broad spectrum of weedgrases and broad-leaved weeds can be achieved. In barley, for example, agood safener action for the herbicide mesosulfuron-methyl could beachieved using the compounds Nos. 1, 2, 3, 5, 7, 9, 10, 13, 14, 22, 25,26, 30, 34, 36, 40, 57, 64, 66, 79, 100, 101, 102, 105, 114, 115, 116,117, 119, 123, 124, 128, 130, 134, 136, 138, 140, 146, 148, 153, 154,155, 157, 163, 165, 168, 169, 171, 178, 193, 194, 214, 341, 342, 344,345, 346, 382, 384, 392, 398, 405, 407, 455, 457, 489, 496, 498, 571,909, 910, 911, 913, 943, 950, 960, 1023, 1026, 1029, 1030, 1201, 1481,1487, 1598, 1599, 1600, 1636, 1907.

In corn, for example, a good safener action for the herbicidetembotrione could be achieved using the following compounds from Table1: 4, 6, 9, 10, 14, 24, 32, 34, 36, 43, 64, 66, 71, 75, 79, 105, 114,118, 140, 146, 148, 153, 169, 178, 210, 214, 345, 51, 95, 341, 456, 457,489, 496, 498, 909, 911, 913, 943, 960, 1026, 1139, 1368, 1371, 1485,1488, 1596, 1597, 1598, 1599, 1600, 1604, 1619, 1625, 1629, 1636, 1638,1646, 1758.

In rice, for example, the following compounds from Table 1 achieved goodsafener action for fenoxaprop-P-ethyl and thiencarbazone orthiencarbazone-methyl: 1, 2, 3, 4, 9, 16, 20, 22, 34, 41, 47, 54, 57,75, 76, 79, 80, 81, 101, 103, 105, 114, 115, 117, 118, 120, 127, 128,130, 153, 154, 157, 162, 165, 169, 171, 178, 218, 271, 341, 342, 344,345, 346, 350, 355, 392, 398, 405, 407, 456, 973, 1482, 1596, 1597,1598, 1600, 1603, 1609, 1625, 1638, 1646, 1659.

3.3 Pre-Emergence Herbicide Action and Safener Action

Seeds or rhizome pieces of monocotyledonous and dicotyledonous weedplants and crop plants were placed in sandy loam soil in plastic potsand covered with soil. The herbicide/safener active compoundcombinations according to the invention, formulated as suspensionemulsion concentrates, and in parallel tests the individual activecompounds formulated in a corresponding manner, were then, at variousdosages at a water application rate of 600 to 800 l/ha (converted),applied to the surface of the covering soil.

After the treatment, the pots were placed in the greenhouse and keptunder good growth conditions for the weeds and the crop plants. Visualscoring of the plant damage or emergence damage was carried out afterthe test plants had emerged after a test period of 3 to 4 weeks, incomparison to untreated controls. The test results showed that thecompounds according to the invention prevented or reduced herbicidedamage to the crop plants without reducing, or reducing substantially,the herbicide action against the harmful plants.

For example, example Nos. 2, 19, 39, 72, 104, 122, 155, 193, 194, 217,232, 271, 341, 380, 392, 1368, 1597, 1625, 1636 of Table 1 showed in thetest in combination with the herbicide isoxaflutol a good safener actionin corn. The herbicidal action of the herbicidally active compounds usedwas not adversely affected. Accordingly, in many cases, the safeners,combined with herbicides, are suitable for the selective control ofhermful plants in the pre-emergence treatment of crops of useful plants.

3.4 Seed Treatment

Seeds of crop plants were mixed in bottles with the safeners accordingto the invention, formulated as suspension or emulsion concentrates, andwater, and the mixture was shaken well so that the seeds were coatedevenly with the formulation of the safener in question. The seeds or theemerged plants were then tested with herbicides in the pre- orpost-emergence method according to the tests of examples 3.3 and 3.2,respectively.

In the treatment of seed, too, the safeners showed good activity. Theherbicidal action of the herbicidally active compounds used was notadversely affected.

Having thus described in detail various embodiments of the presentinvention, it is to be understood that the invention defined by theabove paragraphs is not to be limited to particular details set forth inthe above description as many apparent variations thereof are possiblewithout departing from the spirit or scope of the present invention.

1. A method for protecting useful plants against phytotoxic side effectsof agrochemicals, which comprises applying an effective amount of one ormore of the formula (I) or salts thereof,

in which R¹ is a (C₁-C₆)-haloalkyl radical and R² is hydrogen or halogenand R³ is hydrogen, (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or(C₂-C₁₆)-alkynyl, where each of the 3 last mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted, phenyl, which is unsubstituted orsubstituted, and heterocyclyl, which is unsubstituted or substituted, or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl whichis condensed at one side of the ring to a 4- to 6-membered saturated orunsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl which is condensedat one side of the ring to a 4- to 6-membered saturated or unsaturatedcarbocyclic ring, where each of the 4 last mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,[(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,(C₃-C₆)-cycloalkyl, which is unsubstituted or substituted, phenyl, whichis unsubstituted or substituted, and heterocyclyl, which isunsubstituted or substituted,  and R⁴ is (C₁-C₁₆)-alkyl,(C₂-C₁₆)-alkenyl or (C₂-C₁₆)-alkynyl, where each of the 3 last mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, cyano,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted, phenyl, which is unsubstituted orsubstituted, and heterocyclyl, which is unsubstituted or substituted, or (C₃-C₆)-cycloalkyl, (C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl whichis condensed at one side of the ring to a 4- to 6-membered saturated orunsaturated carbocyclic ring, or (C₄-C₆)-cycloalkenyl which is condensedat one side of the ring to a 4- to 6-membered saturated or unsaturatedcarbocyclic ring, where each of the 4 last mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy,(C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino,[(C₁-C₄)-alkoxy]-carbonyl, [(C₁-C₄)-haloalkoxy]-carbonyl,(C₃-C₆)-cycloalkyl, which is unsubstituted or substituted, phenyl, whichis unsubstituted or substituted, and heterocyclyl, which isunsubstituted or substituted,  or R³ is (C₁-C₄)-alkoxy,(C₂-C₄)-alkenyloxy, (C₂-C₆)-alkynyloxy or (C₂-C₄)-haloalkoxy  and R⁴ ishydrogen or (C₁-C₄)-alkyl  or R³ and R⁴ together with the directlyattached nitrogen atom are a four- to eight-membered heterocyclic ringwhich, in addition to the nitrogen atom, may also comprise furtherhetero ring atoms, and which is unsubstituted or substituted by one ormore radicals selected from the group consisting of halogen, cyano,nitro, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy and (C₁-C₄)-alkylthio,  or R³ and R⁴ together withthe directly attached nitrogen atom are the group —N═CR 5-NR⁶R⁷ in which R⁵ is hydrogen or (C₁-C₆)-alkyl, and  R⁶, R⁷ independently of oneanother are hydrogen or (C₁-C₄)-alkyl, or  R⁶ and R⁷ together with thedirectly attached nitrogen atom form a five- to seven-memberedheterocyclic ring,  or R¹ is a (C₁-C₆)-haloalkyl radical, R² is halogen,R³ is hydrogen and R⁴ is hydrogen  or R¹ is a radical of the formulaCF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃, CFHCF₃, CF(CF₃)₂,CH(CF₃)₂, CF₂CF₂CF₃, or C(CH₃)₂F, R² is hydrogen, R³ is hydrogen and R⁴is hydrogen, before, after or simultaneously with the agrochemicals tothe plants, parts of the plants, the plant seeds or seed of the plants.2. The method as claimed in claim 1 wherein R³ is hydrogen,(C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl, where each of the3 last mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, cyano,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl,phenyl, which is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and(C₁-C₄)-alkylthio, and heterocyclyl, which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,  or (C₃-C₆)-cycloalkyl,(C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl which is condensed at one sideof the ring to a 4- to 6-membered saturated or unsaturated carbocyclicring, or (C₄-C₆)-cycloalkenyl which is condensed at one side of the ringto a 4- to 6-membered saturated or unsaturated carbocyclic ring, whereeach of the 4 last mentioned radicals is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,hydroxyl, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl,phenyl, which is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and(C₁-C₄)-alkylthio, and heterocyclyl, which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo, and R⁴ is (C₁-C₁₀)-alkyl,(C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl, where each of the 3 last mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, hydroxyl, cyano,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl,phenyl, which is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and(C₁-C₄)-alkylthio, and heterocyclyl, which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,  or (C₃-C₆)-cycloalkyl,(C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl which is condensed at one sideof the ring to a 4- to 6-membered saturated or unsaturated carbocyclicring, or (C₄-C₆)-cycloalkenyl which is condensed at one side of the ringto a 4- to 6-membered saturated or unsaturated carbocyclic ring, whereeach of the 4 last mentioned radicals is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,hydroxyl, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl,phenyl, which is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and(C₁-C₄)-alkylthio, and heterocyclyl, which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo.
 3. The method as claimedin claim 1 wherein R³ is hydrogen, (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or(C₂-C₁₀)-alkynyl, where each of the 3 last mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl,phenyl, which is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and(C₁-C₄)-alkylthio, and heterocyclyl, which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,  or (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl which is condensed at one side of the ring to a 4- to6-membered saturated or unsaturated carbocyclic ring, where each of the2 last mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of (C₁-C₄)-alkyl, and R⁴ is(C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl, where each of the3 last mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of halogen, hydroxyl, cyano,(C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, (C₁-C₄)-alkyl and (C₁-C₄)-haloalkyl,phenyl, which is unsubstituted or substituted by one or more radicalsselected from the group consisting of halogen, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and(C₁-C₄)-alkylthio, and heterocyclyl, which is unsubstituted orsubstituted by one or more radicals selected from the group consistingof halogen, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and oxo,  or (C₃-C₆)-cycloalkyl or(C₃-C₆)-cycloalkyl which is condensed at one side of the ring to a 4- to6-membered saturated or unsaturated carbocyclic ring, where each of the2 last mentioned radicals is unsubstituted or substituted by one or moreradicals selected from the group consisting of (C₁-C₄)-alkyl.
 4. Themethod as claimed in claim 1 wherein R³ is hydrogen, (C₁-C₁₀)-alkyl,(C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl, where each of the 3 last mentionedradicals is unsubstituted or substituted by one or more radicalsselected from the group consisting of (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and [(C₁-C₄)-alkoxy]-carbonyl, andR⁴ is (C₁-C₁₀)-alkyl, (C₂-C₁₀)-alkenyl or (C₂-C₁₀)-alkynyl, where eachof the 3 last mentioned radicals is unsubstituted or substituted by oneor more radicals selected from the group consisting of (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio and [(C₁-C₄)-alkoxy]-carbonyl. 5.The method as claimed in claim 1, wherein R¹ is CF₃, CF₂C₁, CF₂H,CF₂CF₃, CF₂CF₂H, CF₂CF₂C₁, CF₂CF₂CF₃ or C(CH₃)₂F and R² is hydrogen orhalogen.
 6. The method as claimed in claim 1, wherein R¹ is a(C₁-C₆)-haloalkyl radical, R² is halogen, R³ is hydrogen, and R⁴ ishydrogen.
 7. The method as claimed in claim 1, wherein R¹ is a radicalof the formula CF₂C₁, CF₂H, CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl, CFClCF₃, CFHCF₃,CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃, or C(CH₃)₂F, R² is hydrogen, R³ ishydrogen and R⁴ is hydrogen.
 8. The method as claimed in any of claim 1,wherein one or more compounds of the formula (I) or salts thereof areused together with one or more agrochemicals which, applied on theirown, cause damage to the useful plants, optionally in the presence offormulation auxiliaries.
 9. The method as claimed in claim 1, whereinthe application is by the post-emergence method.
 10. The method asclaimed in claim 1, wherein the application of the compound of theformula (I) or a salt thereof is by treating the plant seeds or seed ofthe plants.
 11. The method as claimed in claim 1, wherein theapplication is by the pre-emergence method.
 12. A method for theselective control of harmful plants in crops of useful plants, whichcomprises applying an effective amount of one or more compounds of theformula (I) or salts thereof as defined in claim 1 before, after orsimultaneously with one or more herbicides to the plants, parts ofplants, plant seeds or seed of the plants.
 13. The method as claimed inclaim 12, which comprises treating the seed of the plants with one ormore compounds of the formula (I) or salts thereof and applying theherbicide after sowing by the pre-emergence method or by thepost-emergence method.
 14. A compound of the formula (I) or a saltthereof,

in which R¹ is a (C₁-C₆)-haloalkyl radical and R² is hydrogen or halogenand R³ is hydrogen, (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or(C₂-C₁₆)-alkynyl, where each of the 3 last mentioned radicals isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, hydroxyl, cyano, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl and[(C₁-C₄)-haloalkoxy]-carbonyl  or (C₃-C₆)-cycloalkyl,(C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl which is condensed at one sideof the ring to a 4- to 6-membered saturated or unsaturated carbocyclicring, or (C₄-C₆)-cycloalkenyl which is condensed at one side of the ringto a 4- to 6-membered saturated or unsaturated carbocyclic ring, whereeach of the 4 last mentioned radicals is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,hydroxyl, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted, phenyl, which is unsubstituted orsubstituted, and heterocyclyl, which is unsubstituted or substituted, and R⁴ is (C₁-C₁₆)-alkyl, (C₂-C₁₆)-alkenyl or (C₂-C₁₆)-alkynyl, whereeach of the 3 last mentioned radicals is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,hydroxyl, cyano, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio,(C₁-C₄)-alkylamino, di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyland [(C₁-C₄)-haloalkoxy]-carbonyl,  or (C₃-C₆)-cycloalkyl,(C₄-C₆)-cycloalkenyl, (C₃-C₆)-cycloalkyl which is condensed at one sideof the ring to a 4- to 6-membered saturated or unsaturated carbocyclicring, or (C₄-C₆)-cycloalkenyl which is condensed at one side of the ringto a 4- to 6-membered saturated or unsaturated carbocyclic ring, whereeach of the 4 last mentioned radicals is unsubstituted or substituted byone or more radicals selected from the group consisting of halogen,hydroxyl, cyano, (C₁-C₄)-alkyl, (C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy,(C₁-C₄)-haloalkoxy, (C₁-C₄)-alkylthio, (C₁-C₄)-alkylamino,di[(C₁-C₄)-alkyl]-amino, [(C₁-C₄)-alkoxy]-carbonyl,[(C₁-C₄)-haloalkoxy]-carbonyl, (C₃-C₆)-cycloalkyl, which isunsubstituted or substituted, phenyl, which is unsubstituted orsubstituted, and heterocyclyl, which is unsubstituted or substituted, or R³ is (C₁-C₄)-alkoxy, (C₂-C₄)-alkenyloxy, (C₂-C₆)-alkynyloxy or(C₂-C₄)-haloalkoxy and R⁴ is hydrogen or (C₁-C₄)-alkyl  or R³ and R⁴together with the directly attached nitrogen atom are a four- toeight-membered heterocyclic ring which, in addition to the nitrogenatom, may also comprise further hetero ring atoms, and which isunsubstituted or substituted by one or more radicals selected from thegroup consisting of halogen, cyano, nitro, (C₁-C₄)-alkyl,(C₁-C₄)-haloalkyl, (C₁-C₄)-alkoxy, (C₁-C₄)-haloalkoxy and(C₁-C₄)-alkylthio,  or R³ and R⁴ together with the directly attachednitrogen atom are the group —N═CR⁵—NR⁶R⁷ in which  R⁵ is hydrogen or(C₁-C₆)-alkyl, and  R⁶, R⁷ independently of one another are hydrogen or(C₁-C₄)-alkyl, or  R⁶ and R⁷ together with the directly attachednitrogen atom form a five- to seven-membered heterocyclic ring,  or R¹is a (C₁-C₆)-haloalkyl radical, R² is halogen, R³ is hydrogen and R⁴ ishydrogen  or R¹ is a radical of the formula CF₂CF₃, CF₂CF₂H, CF₂CF₂Cl,CFClCF₃, CFHCF₃, CF(CF₃)₂, CH(CF₃)₂, CF₂CF₂CF₃, or C(CH₃)₂F, R² ishydrogen, R³ is hydrogen and R⁴ is hydrogen.
 15. A process for preparingcompounds of the general formula (I) or salts thereof as defined inclaim 14, which comprises (a) reacting a carboxylic acid of the generalformula (II)

in which R¹ and R² are as defined for the compound of the formula (I) tobe prepared, with an amine of the formula (III) or a salt thereof,

in which R³ and R⁴ are as defined for the compound of the formula (I) tobe prepared, to give the compound of the formula (I) or (b) reacting acarboxylic ester of the general formula (IV)

in which R¹ and R² are as defined for the compound of the formula (I) tobe prepared and “Alkyl” is an alkyl radical, with an amine of theformula (III) or a salt thereof,

in which R³ and R⁴ are as defined for the compound of the formula (I) tobe prepared, to give the compound of the formula (I) or (c) reacting acarbonyl halide or a carboxylic anhydride of the general formula (V),

in which R¹ and R² are as defined for the compound of the formula (I) tobe prepared and Hal is a halogen atom or an acyloxy radical with anamine of the formula (III) or a salt thereof,

in which R³ and R⁴ are as defined for the compound of the formula (I) tobe prepared to give the compound of the formula (I), or (d) if R³ and R⁴in the compound of the formula (I) to be prepared are each hydrogen,reacting a compound of the formula (VI),

in which R¹ is as defined for the compound of the formula (I) to beprepared, and “Alkyl” is an alkyl radical, with malonamide to give thecompound of the formula (I).
 15. A crop protection composition whichcomprises one or more compounds of the formula (I) or salts thereof asdefined in claim 1 and formulation auxiliaries.
 16. A crop protectioncomposition which comprises one or more compounds of the formula (I) orsalts thereof as defined in claim 1 and one or more agrochemicals and,optionally, formulation auxiliaries.